David O'Leary (Oct 1998 - Jun 2002)
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David O'Leary (Oct 1998 - Jun 2002)
Debut: 03/10/1998 - Leicester City (H)
Games: 203 | Win%: 49.75%
Debut: 03/10/1998 - Leicester City (H)
David O'Leary was promoted from assistant to manager of Leeds United in 1998 following George Graham's departure. His youthful energy and belief in emerging talent led to one of the most exciting periods in modern club history. O'Leary built a team around young stars like Harry Kewell, Alan Smith, and Jonathan Woodgate, playing an adventurous style that endeared them to fans. Under his guidance, Leeds reached the UEFA Cup semi-final in 2000 and the Champions League semi-final in 2001.
However, behind the scenes, heavy spending and boardroom pressure created financial instability. When Leeds failed to qualify for the Champions League again, the cost of previous investments became a burden. O'Leary was sacked in 2002 despite maintaining the club's competitiveness. He later managed Aston Villa but never replicated his early success. For many supporters, his era remains a bittersweet mix of ambition, drama, and what might have been.
| Record | P | W | D | L | F | A | GD | PPG* | Win% | |
| League | 145 | 75 | 34 | 36 | 229 | 153 | 76 | 1.79 | 51.72% | |
| FA Cup | 11 | 5 | 2 | 4 | 20 | 14 | 6 | - | 45.45% | |
| League Cup | 7 | 3 | 1 | 3 | 11 | 7 | 4 | - | 42.86% | |
| Europe | 40 | 18 | 10 | 12 | 60 | 43 | 17 | - | 45.00% | |
| TOTAL | 203 | 101 | 47 | 55 | 320 | 217 | 103 | - | 49.75% | |
* Points per game based on 3 points for a win as introduced from the 1981–1982 season onwards
| Honours | Season | |
| UEFA Cup Semi Finalists | 1999-2000 | |
| Champions League Semi Finalists | 2000-2001 |
| League | Venue |
Date | Score | |||
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Leicester City | H | Elland Road |
03/10/1998 | 0 : 1 | L |
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Nottingham Forest | A | City Ground |
17/10/1998 | 1 : 1 | D |
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Chelsea | H | Elland Road |
25/10/1998 | 0 : 0 | D |
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Derby County | A | Pride Park |
31/10/1998 | 2 : 2 | D |
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Sheffield Wednesday | H | Elland Road |
08/11/1998 | 2 : 1 | W |
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Liverpool | A | Anfield |
14/11/1998 | 3 : 1 | W |
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Charlton Athletic | H | Elland Road |
21/11/1998 | 4 : 1 | W |
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Manchester United | A | Old Trafford |
29/11/1998 | 2 : 3 | L |
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West Ham United | H | Elland Road |
05/12/1998 | 4 : 0 | W |
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Coventry City | H | Elland Road |
14/12/1998 | 2 : 0 | W |
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Arsenal | A | Highbury |
20/12/1998 | 1 : 3 | L |
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Newcastle United | A | St James Park |
26/12/1998 | 3 : 0 | W |
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Wimbledon | H | Elland Road |
29/12/1998 | 2 : 2 | D |
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Blackburn Rovers | A | Ewood Park |
09/01/1999 | 0 : 1 | L |
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Middlesbrough | H | Elland Road |
16/01/1999 | 2 : 0 | W |
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Southampton | A | The Dell |
30/01/1999 | 0 : 3 | L |
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Newcastle United | H | Elland Road |
06/02/1999 | 0 : 1 | L |
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Aston Villa | A | Villa Park |
17/02/1999 | 2 : 1 | W |
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Everton | H | Elland Road |
20/02/1999 | 1 : 0 | W |
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Leicester City | A | Filbert Street |
01/03/1999 | 2 : 1 | W |
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Tottenham Hotspur | H | Elland Road |
10/03/1999 | 2 : 0 | W |
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Sheffield Wednesday | A | Hillsborough |
13/03/1999 | 2 : 0 | W |
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Derby County | H | Elland Road |
20/03/1999 | 4 : 1 | W |
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Nottingham Forest | H | Elland Road |
03/04/1999 | 3 : 1 | W |
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Liverpool | H | Elland Road |
12/04/1999 | 0 : 0 | D |
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Charlton Athletic | A | The Valley |
17/04/1999 | 1 : 1 | D |
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Manchester United | H | Elland Road |
25/04/1999 | 1 : 1 | D |
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West Ham United | A | Upton Park |
01/05/1999 | 5 : 1 | W |
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Chelsea | A | Stamford Bridge |
05/05/1999 | 0 : 1 | L |
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Arsenal | H | Elland Road |
11/05/1999 | 1 : 0 | W |
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Coventry City | A | Highfield Road |
16/05/1999 | 2 : 2 | D |
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Derby County | H | Elland Road |
07/08/1999 | 0 : 0 | D |
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Southampton | A | The Dell |
11/08/1999 | 3 : 0 | W |
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Manchester United | A | Old Trafford |
14/08/1999 | 0 : 2 | L |
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Sunderland | H | Elland Road |
21/08/1999 | 2 : 1 | W |
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Liverpool | H | Elland Road |
23/08/1999 | 1 : 2 | L |
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Tottenham Hotspur | A | White Hart Lane |
28/08/1999 | 2 : 1 | W |
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Coventry City | A | Highfield Road |
11/09/1999 | 4 : 3 | W |
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Middlesbrough | H | Elland Road |
19/09/1999 | 2 : 0 | W |
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Newcastle United | H | Elland Road |
25/09/1999 | 3 : 2 | W |
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Watford | A | Vicarage Road |
03/10/1999 | 2 : 1 | W |
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Sheffield Wednesday | H | Elland Road |
16/10/1999 | 2 : 0 | W |
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Everton | A | Goodison Park |
24/10/1999 | 4 : 4 | D |
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West Ham United | H | Elland Road |
30/10/1999 | 1 : 0 | W |
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Wimbledon | A | Selhurst Park |
07/11/1999 | 0 : 2 | L |
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Bradford City | H | Elland Road |
20/11/1999 | 2 : 1 | W |
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Southampton | H | Elland Road |
28/11/1999 | 1 : 0 | W |
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Derby County | A | Pride Park |
05/12/1999 | 1 : 0 | W |
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Chelsea | A | Stamford Bridge |
19/12/1999 | 2 : 0 | W |
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Leicester City | H | Elland Road |
26/12/1999 | 2 : 1 | W |
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Arsenal | A | Highbury |
28/12/1999 | 0 : 2 | L |
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Aston Villa | H | Elland Road |
03/01/2000 | 1 : 2 | L |
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Sunderland | A | Stadium Of Light |
23/01/2000 | 2 : 1 | W |
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Liverpool | A | Anfield |
05/02/2000 | 1 : 3 | L |
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Tottenham Hotspur | H | Elland Road |
12/02/2000 | 1 : 0 | W |
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Manchester United | H | Elland Road |
20/02/2000 | 0 : 1 | L |
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Middlesbrough | A | Riverside Stadium |
26/02/2000 | 0 : 0 | D |
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Coventry City | H | Elland Road |
05/03/2000 | 3 : 0 | W |
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Bradford City | A | Valley Parade |
12/03/2000 | 2 : 1 | W |
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Wimbledon | H | Elland Road |
19/03/2000 | 4 : 1 | W |
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Leicester City | H | Elland Road |
26/03/2000 | 1 : 2 | L |
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Chelsea | H | Elland Road |
01/04/2000 | 0 : 1 | L |
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Aston Villa | A | Villa Park |
09/04/2000 | 0 : 1 | L |
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Arsenal | H | Elland Road |
16/04/2000 | 0 : 4 | L |
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Newcastle United | A | St James Park |
23/04/2000 | 2 : 2 | D |
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Sheffield Wednesday | A | Hillsborough |
30/04/2000 | 3 : 0 | W |
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Watford | H | Elland Road |
03/05/2000 | 3 : 1 | W |
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Everton | H | Elland Road |
08/05/2000 | 1 : 1 | D |
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West Ham United | A | Upton Park |
14/05/2000 | 0 : 0 | D |
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Everton | H | Elland Road |
19/08/2000 | 2 : 0 | W |
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Middlesbrough | A | Riverside Stadium |
26/08/2000 | 2 : 1 | W |
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Manchester City | H | Elland Road |
05/09/2000 | 1 : 2 | L |
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Coventry City | A | Highfield Road |
09/09/2000 | 0 : 0 | D |
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Ipswich Town | H | Elland Road |
16/09/2000 | 1 : 2 | L |
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Derby County | A | Pride Park |
23/09/2000 | 1 : 1 | D |
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Tottenham Hotspur | H | Elland Road |
30/09/2000 | 4 : 3 | W |
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Charlton Athletic | H | Elland Road |
14/10/2000 | 3 : 1 | W |
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Manchester United | A | Old Trafford |
21/10/2000 | 0 : 3 | L |
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Bradford City | A | Valley Parade |
29/10/2000 | 1 : 1 | D |
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Liverpool | H | Elland Road |
04/11/2000 | 4 : 3 | W |
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Chelsea | A | Stamford Bridge |
12/11/2000 | 1 : 1 | D |
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West Ham United | H | Elland Road |
18/11/2000 | 0 : 1 | L |
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Arsenal | H | Elland Road |
26/11/2000 | 1 : 0 | W |
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Leicester City | A | Filbert Street |
02/12/2000 | 1 : 3 | L |
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Southampton | A | The Dell |
09/12/2000 | 0 : 1 | L |
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Sunderland | H | Elland Road |
16/12/2000 | 2 : 0 | W |
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Aston Villa | H | Elland Road |
23/12/2000 | 1 : 2 | L |
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Newcastle United | A | St James Park |
26/12/2000 | 1 : 2 | L |
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Middlesbrough | H | Elland Road |
01/01/2001 | 1 : 1 | D |
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Manchester City | A | Maine Road |
13/01/2001 | 4 : 0 | W |
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Newcastle United | H | Elland Road |
20/01/2001 | 1 : 3 | L |
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Aston Villa | A | Villa Park |
24/01/2001 | 2 : 1 | W |
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Coventry City | H | Elland Road |
31/01/2001 | 1 : 0 | W |
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Ipswich Town | A | Portman Road |
03/02/2001 | 2 : 1 | W |
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Everton | A | Goodison Park |
07/02/2001 | 2 : 2 | D |
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Derby County | H | Elland Road |
10/02/2001 | 0 : 0 | D |
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Tottenham Hotspur | A | White Hart Lane |
24/02/2001 | 2 : 1 | W |
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Manchester United | H | Elland Road |
03/03/2001 | 1 : 1 | D |
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Charlton Athletic | A | The Valley |
17/03/2001 | 2 : 1 | W |
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Sunderland | A | Stadium Of Light |
31/03/2001 | 2 : 0 | W |
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Southampton | H | Elland Road |
07/04/2001 | 2 : 0 | W |
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Liverpool | A | Anfield |
13/04/2001 | 2 : 1 | W |
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West Ham United | A | Upton Park |
21/04/2001 | 2 : 0 | W |
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Chelsea | H | Elland Road |
28/04/2001 | 2 : 0 | W |
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Arsenal | A | Highbury |
05/05/2001 | 1 : 2 | L |
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Bradford City | H | Elland Road |
13/05/2001 | 6 : 1 | W |
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Leicester City | H | Elland Road |
19/05/2001 | 3 : 1 | W |
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Southampton | H | Elland Road |
18/08/2001 | 2 : 0 | W |
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Arsenal | A | Highbury |
21/08/2001 | 2 : 1 | W |
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West Ham United | A | Upton Park |
25/08/2001 | 0 : 0 | D |
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Bolton Wanderers | H | Elland Road |
08/09/2001 | 0 : 0 | D |
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Charlton Athletic | A | The Valley |
16/09/2001 | 2 : 0 | W |
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Derby County | H | Elland Road |
23/09/2001 | 3 : 0 | W |
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Ipswich Town | A | Portman Road |
30/09/2001 | 2 : 1 | W |
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Liverpool | A | Anfield |
13/10/2001 | 1 : 1 | D |
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Chelsea | H | Elland Road |
21/10/2001 | 0 : 0 | D |
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Manchester United | A | Old Trafford |
27/10/2001 | 1 : 1 | D |
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Tottenham Hotspur | H | Elland Road |
04/11/2001 | 2 : 1 | W |
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Sunderland | A | Stadium Of Light |
18/11/2001 | 0 : 2 | L |
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Aston Villa | H | Elland Road |
25/11/2001 | 1 : 1 | D |
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Fulham | A | Craven Cottage |
02/12/2001 | 0 : 0 | D |
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Blackburn Rovers | A | Ewood Park |
09/12/2001 | 2 : 1 | W |
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Leicester City | H | Elland Road |
16/12/2001 | 2 : 2 | D |
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Everton | H | Elland Road |
19/12/2001 | 3 : 2 | W |
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Newcastle United | H | Elland Road |
22/12/2001 | 3 : 4 | L |
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Bolton Wanderers | A | Reebok Stadium |
26/12/2001 | 3 : 0 | W |
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Southampton | A | St Marys Stadium |
29/12/2001 | 1 : 0 | W |
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West Ham United | H | Elland Road |
01/01/2002 | 3 : 0 | W |
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Newcastle United | A | St James Park |
12/01/2002 | 1 : 3 | L |
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Arsenal | H | Elland Road |
20/01/2002 | 1 : 1 | D |
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Chelsea | A | Stamford Bridge |
30/01/2002 | 0 : 2 | L |
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Liverpool | H | Elland Road |
03/02/2002 | 0 : 4 | L |
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Middlesbrough | A | Riverside Stadium |
09/02/2002 | 2 : 2 | D |
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Charlton Athletic | H | Elland Road |
24/02/2002 | 0 : 0 | D |
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Everton | A | Goodison Park |
03/03/2002 | 0 : 0 | D |
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Ipswich Town | H | Elland Road |
06/03/2002 | 2 : 0 | W |
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Blackburn Rovers | H | Elland Road |
17/03/2002 | 3 : 1 | W |
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Leicester City | A | Filbert Street |
23/03/2002 | 2 : 0 | W |
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Manchester United | H | Elland Road |
30/03/2002 | 3 : 4 | L |
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Tottenham Hotspur | A | White Hart Lane |
01/04/2002 | 1 : 2 | L |
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Sunderland | H | Elland Road |
07/04/2002 | 2 : 0 | W |
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Aston Villa | A | Villa Park |
13/04/2002 | 1 : 0 | W |
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Fulham | H | Elland Road |
20/04/2002 | 0 : 1 | L |
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Derby County | A | Pride Park |
27/04/2002 | 1 : 0 | W |
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Middlesbrough | H | Elland Road |
11/05/2002 | 1 : 0 | W |
| FA Cup | Venue |
Date | Score | |||
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Rushden & Diamonds FA Cup 3rd Round |
A | Nene Park |
02/01/1999 | 0 : 0 | D |
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Rushden & Diamonds FA Cup 3rd Round Replay |
H | Elland Road |
13/01/1999 | 3 : 1 | W |
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Portsmouth FA Cup 4th Round |
A | Fratton Park |
23/01/1999 | 5 : 1 | W |
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Tottenham Hotspur FA Cup 5th Round |
H | Elland Road |
13/02/1999 | 1 : 1 | D |
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Tottenham Hotspur FA Cup 5th Round Replay |
A | White Hart Lane |
24/02/1999 | 0 : 2 | L |
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Port Vale FA Cup 3rd Round |
H | Elland Road |
12/12/1999 | 2 : 0 | W |
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Manchester City FA Cup 4th Round |
A | Maine Road |
09/01/2000 | 5 : 2 | W |
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Aston Villa FA Cup 5th Round |
A | Villa Park |
30/01/2000 | 2 : 3 | L |
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Barnsley FA Cup 3rd Round |
H | Elland Road |
06/01/2001 | 1 : 0 | W |
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Liverpool FA Cup 4th Round |
H | Elland Road |
27/01/2001 | 0 : 2 | L |
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Cardiff City FA Cup 3rd Round |
A | Ninian Park |
06/01/2002 | 1 : 2 | L |
| League Cup | Venue |
Date | Score | |||
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Bradford City Worthington Cup 3rd Round |
H | Elland Road |
28/10/1998 | 1 : 0 | W |
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Leicester City Worthington Cup 4th Round |
A | Filbert Street |
11/11/1998 | 1 : 2 | L |
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Blackburn Rovers Worthington Cup 3rd Round |
H | Elland Road |
13/10/1999 | 1 : 0 | W |
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Leicester City Worthington Cup 4th Round |
A | Filbert Street |
15/12/1999 | 0 : 0 (2 : 4 p) |
D |
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Tranmere Rovers Worthington Cup 3rd Round |
A | Prenton Park |
31/10/2000 | 2 : 3 | L |
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Leicester City Worthington Cup 3rd Round |
A | Filbert Street |
09/10/2001 | 6 : 0 | W |
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Chelsea Worthington Cup 4th Round |
H | Elland Road |
28/11/2001 | 0 : 2 | L |
| Europe | Venue |
Date | Score | |||
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Roma UEFA Cup 2nd Round 1st Leg |
A | Olympic Stadium |
20/10/1998 | 0 : 1 | L |
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Roma UEFA Cup 2nd Round 2nd Leg |
H | Elland Road |
03/11/1998 | 0 : 0 | D |
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Partizan Belgrade UEFA Cup 1st Round 1st Leg |
A | Abe Lenstra Stadium |
14/09/1999 | 3 : 1 | W |
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Partizan Belgrade UEFA Cup 1st Round 2nd Leg |
H | Elland Road |
30/09/1999 | 1 : 0 | W |
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Lokomotiv Moscow UEFA Cup 2nd Round 1st Leg |
H | Elland Road |
21/10/1999 | 4 : 1 | W |
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Lokomotiv Moscow UEFA Cup 2nd Round 2nd Leg |
A | Lokomotiv Stadium |
04/11/1999 | 3 : 0 | W |
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Spartak Moscow UEFA Cup 3rd Round 1st Leg |
A | The Georgi Asparuchov Stadium |
02/12/1999 | 1 : 2 | L |
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Spartak Moscow UEFA Cup 3rd Round 2nd Leg |
H | Elland Road |
09/12/1999 | 1 : 0 | W |
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Roma UEFA Cup 4th Round 1st Leg |
A | Olympic Stadium |
02/03/2000 | 0 : 0 | D |
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Roma UEFA Cup 4th Round 2nd Leg |
H | Elland Road |
09/03/2000 | 1 : 0 | W |
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Slavia Prague UEFA Cup Quarter Final 1st Leg |
H | Elland Road |
16/03/2000 | 3 : 0 | W |
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Slavia Prague UEFA Cup Quarter Final 2nd Leg |
A | Strahov Stadium |
26/03/2000 | 1 : 2 | L |
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Galatasaray UEFA Cup Semi Final 1st Leg |
A | Ali Semi Yen |
06/04/2000 | 0 : 2 | L |
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Galatasaray UEFA Cup Semi Final 2nd Leg |
H | Elland Road |
20/04/2000 | 2 : 2 | D |
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1860 Munich Champions League 3rd Qualifying Round 1st Leg |
H | Elland Road |
09/08/2000 | 2 : 1 | W |
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1860 Munich Champions League 3rd Qualifying Round 2nd Leg |
A | Olympic Stadium |
23/08/2000 | 1 : 0 | W |
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Barcelona Champions Leaguue Phase 1 Group H |
A | Nou Camp |
13/09/2000 | 0 : 4 | L |
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AC Milan Champions League Phase 1 Group H |
H | Elland Road |
19/09/2000 | 1 : 0 | W |
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Besiktas Champions League Phase 1 Group H |
H | Elland Road |
26/09/2000 | 6 : 0 | W |
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Besiktas Champions League Phase 1 Group H |
A | Inonu Stadium |
18/10/2000 | 0 : 0 | D |
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Barcelona Champions League Phase 1 Group H |
H | Elland Road |
24/10/2000 | 1 : 1 | D |
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AC Milan Champions League Phase 1 Group H |
A | San Siro |
08/11/2000 | 1 : 1 | D |
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Real Madrid Champions League Phase 2 Group D |
H | Elland Road |
22/11/2000 | 0 : 2 | L |
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Lazio Champions League Phase 2 Group D |
A | Olympic Stadium |
05/12/2000 | 1 : 0 | W |
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Anderlecht Champions League Phase 2 Group D |
H | Elland Road |
13/02/2001 | 2 : 1 | W |
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Anderlecht Champions League Phase 2 Group D |
A | Vanden Stock Stadium |
21/02/2001 | 4 : 1 | W |
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Real Madrid Champions League Phase 2 Group D |
A | Santiago Bernabeu |
06/03/2001 | 2 : 3 | L |
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Lazio Champions League Phase 2 Group D |
H | Elland Road |
14/03/2001 | 3 : 3 | D |
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Deportivo La Coruna Champions League Quarter Final 1st Leg |
H | Elland Road |
04/04/2001 | 3 : 0 | W |
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Deportivo La Coruna Champions League Quarter Final 2nd Leg |
A | Riazor |
17/04/2001 | 0 : 2 | L |
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Valencia Champions League Semi Final 1st Leg |
H | Elland Road |
02/05/2001 | 0 : 0 | D |
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Valencia Champions League Semi Final 2nd Leg |
A | Mestalla |
08/05/2001 | 0 : 3 | L |
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Maritimo UEFA Cup 1st Round 1st Leg |
A | Estadio Dos Barreiros |
20/09/2001 | 0 : 1 | L |
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Maritimo UEFA Cup 1st Round 2nd Leg |
H | Elland Road |
27/09/2001 | 3 : 0 | W |
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Troyes UEFA Cup 2nd Round 1st Leg |
H | Elland Road |
18/10/2001 | 4 : 2 | W |
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Troyes UEFA Cup 2nd Round 2nd Leg |
A | Stade De L’Aube |
01/11/2001 | 2 : 3 | L |
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Grasshoppers UEFA Cup 3rd Round 1st Leg |
A | Hardtrum Stadium |
22/11/2001 | 2 : 1 | W |
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Grasshoppers UEFA Cup 3rd Round 2nd Leg |
H | Elland Road |
06/12/2001 | 2 : 2 | D |
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PSV Eindhoven UEFA Cup 4th Round 1st Leg |
A | Phillips Stadion |
21/02/2002 | 0 : 0 | D |
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PSV Eindhoven UEFA Cup 4th Round 2nd Leg |
H | Elland Road |
28/02/2002 | 0 : 1 | L |
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