Ireland David O'Leary (Oct 1998 - Jun 2002)

Ireland David O'Leary (Oct 1998 - Jun 2002)

Born: Stoke Newington, London | DOB: 02/05/1958 | Games: 203 | Win%: 49.75%
Debut: 03/10/1998 - Leicester City (H)
Born: Stoke Newington, London | DOB: 02/05/1958
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
Leicester City H
Elland Road
03/10/1998 0 : 1
L
Nottingham Forest A
City Ground
17/10/1998 1 : 1
D
Chelsea H
Elland Road
25/10/1998 0 : 0
D
Derby County A
Pride Park
31/10/1998 2 : 2
D
Sheffield Wednesday H
Elland Road
08/11/1998 2 : 1
W
Liverpool A
Anfield
14/11/1998 3 : 1
W
Charlton Athletic H
Elland Road
21/11/1998 4 : 1
W
Manchester United A
Old Trafford
29/11/1998 2 : 3
L
West Ham United H
Elland Road
05/12/1998 4 : 0
W
Coventry City H
Elland Road
14/12/1998 2 : 0
W
Arsenal A
Highbury
20/12/1998 1 : 3
L
Newcastle United A
St James Park
26/12/1998 3 : 0
W
Wimbledon H
Elland Road
29/12/1998 2 : 2
D
Blackburn Rovers A
Ewood Park
09/01/1999 0 : 1
L
Middlesbrough H
Elland Road
16/01/1999 2 : 0
W
Southampton A
The Dell
30/01/1999 0 : 3
L
Newcastle United H
Elland Road
06/02/1999 0 : 1
L
Aston Villa A
Villa Park
17/02/1999 2 : 1
W
Everton H
Elland Road
20/02/1999 1 : 0
W
Leicester City A
Filbert Street
01/03/1999 2 : 1
W
Tottenham Hotspur H
Elland Road
10/03/1999 2 : 0
W
Sheffield Wednesday A
Hillsborough
13/03/1999 2 : 0
W
Derby County H
Elland Road
20/03/1999 4 : 1
W
Nottingham Forest H
Elland Road
03/04/1999 3 : 1
W
Liverpool H
Elland Road
12/04/1999 0 : 0
D
Charlton Athletic A
The Valley
17/04/1999 1 : 1
D
Manchester United H
Elland Road
25/04/1999 1 : 1
D
West Ham United A
Upton Park
01/05/1999 5 : 1
W
Chelsea A
Stamford Bridge
05/05/1999 0 : 1
L
Arsenal H
Elland Road
11/05/1999 1 : 0
W
Coventry City A
Highfield Road
16/05/1999 2 : 2
D
Derby County H
Elland Road
07/08/1999 0 : 0
D
Southampton A
The Dell
11/08/1999 3 : 0
W
Manchester United A
Old Trafford
14/08/1999 0 : 2
L
Sunderland H
Elland Road
21/08/1999 2 : 1
W
Liverpool H
Elland Road
23/08/1999 1 : 2
L
Tottenham Hotspur A
White Hart Lane
28/08/1999 2 : 1
W
Coventry City A
Highfield Road
11/09/1999 4 : 3
W
Middlesbrough H
Elland Road
19/09/1999 2 : 0
W
Newcastle United H
Elland Road
25/09/1999 3 : 2
W
Watford A
Vicarage Road
03/10/1999 2 : 1
W
Sheffield Wednesday H
Elland Road
16/10/1999 2 : 0
W
Everton A
Goodison Park
24/10/1999 4 : 4
D
West Ham United H
Elland Road
30/10/1999 1 : 0
W
Wimbledon A
Selhurst Park
07/11/1999 0 : 2
L
Bradford City H
Elland Road
20/11/1999 2 : 1
W
Southampton H
Elland Road
28/11/1999 1 : 0
W
Derby County A
Pride Park
05/12/1999 1 : 0
W
Chelsea A
Stamford Bridge
19/12/1999 2 : 0
W
Leicester City H
Elland Road
26/12/1999 2 : 1
W
Arsenal A
Highbury
28/12/1999 0 : 2
L
Aston Villa H
Elland Road
03/01/2000 1 : 2
L
Sunderland A
Stadium Of Light
23/01/2000 2 : 1
W
Liverpool A
Anfield
05/02/2000 1 : 3
L
Tottenham Hotspur H
Elland Road
12/02/2000 1 : 0
W
Manchester United H
Elland Road
20/02/2000 0 : 1
L
Middlesbrough A
Riverside Stadium
26/02/2000 0 : 0
D
Coventry City H
Elland Road
05/03/2000 3 : 0
W
Bradford City A
Valley Parade
12/03/2000 2 : 1
W
Wimbledon H
Elland Road
19/03/2000 4 : 1
W
Leicester City H
Elland Road
26/03/2000 1 : 2
L
Chelsea H
Elland Road
01/04/2000 0 : 1
L
Aston Villa A
Villa Park
09/04/2000 0 : 1
L
Arsenal H
Elland Road
16/04/2000 0 : 4
L
Newcastle United A
St James Park
23/04/2000 2 : 2
D
Sheffield Wednesday A
Hillsborough
30/04/2000 3 : 0
W
Watford H
Elland Road
03/05/2000 3 : 1
W
Everton H
Elland Road
08/05/2000 1 : 1
D
West Ham United A
Upton Park
14/05/2000 0 : 0
D
Everton H
Elland Road
19/08/2000 2 : 0
W
Middlesbrough A
Riverside Stadium
26/08/2000 2 : 1
W
Manchester City H
Elland Road
05/09/2000 1 : 2
L
Coventry City A
Highfield Road
09/09/2000 0 : 0
D
Ipswich Town H
Elland Road
16/09/2000 1 : 2
L
Derby County A
Pride Park
23/09/2000 1 : 1
D
Tottenham Hotspur H
Elland Road
30/09/2000 4 : 3
W
Charlton Athletic H
Elland Road
14/10/2000 3 : 1
W
Manchester United A
Old Trafford
21/10/2000 0 : 3
L
Bradford City A
Valley Parade
29/10/2000 1 : 1
D
Liverpool H
Elland Road
04/11/2000 4 : 3
W
Chelsea A
Stamford Bridge
12/11/2000 1 : 1
D
West Ham United H
Elland Road
18/11/2000 0 : 1
L
Arsenal H
Elland Road
26/11/2000 1 : 0
W
Leicester City A
Filbert Street
02/12/2000 1 : 3
L
Southampton A
The Dell
09/12/2000 0 : 1
L
Sunderland H
Elland Road
16/12/2000 2 : 0
W
Aston Villa H
Elland Road
23/12/2000 1 : 2
L
Newcastle United A
St James Park
26/12/2000 1 : 2
L
Middlesbrough H
Elland Road
01/01/2001 1 : 1
D
Manchester City A
Maine Road
13/01/2001 4 : 0
W
Newcastle United H
Elland Road
20/01/2001 1 : 3
L
Aston Villa A
Villa Park
24/01/2001 2 : 1
W
Coventry City H
Elland Road
31/01/2001 1 : 0
W
Ipswich Town A
Portman Road
03/02/2001 2 : 1
W
Everton A
Goodison Park
07/02/2001 2 : 2
D
Derby County H
Elland Road
10/02/2001 0 : 0
D
Tottenham Hotspur A
White Hart Lane
24/02/2001 2 : 1
W
Manchester United H
Elland Road
03/03/2001 1 : 1
D
Charlton Athletic A
The Valley
17/03/2001 2 : 1
W
Sunderland A
Stadium Of Light
31/03/2001 2 : 0
W
Southampton H
Elland Road
07/04/2001 2 : 0
W
Liverpool A
Anfield
13/04/2001 2 : 1
W
West Ham United A
Upton Park
21/04/2001 2 : 0
W
Chelsea H
Elland Road
28/04/2001 2 : 0
W
Arsenal A
Highbury
05/05/2001 1 : 2
L
Bradford City H
Elland Road
13/05/2001 6 : 1
W
Leicester City H
Elland Road
19/05/2001 3 : 1
W
Southampton H
Elland Road
18/08/2001 2 : 0
W
Arsenal A
Highbury
21/08/2001 2 : 1
W
West Ham United A
Upton Park
25/08/2001 0 : 0
D
Bolton Wanderers H
Elland Road
08/09/2001 0 : 0
D
Charlton Athletic A
The Valley
16/09/2001 2 : 0
W
Derby County H
Elland Road
23/09/2001 3 : 0
W
Ipswich Town A
Portman Road
30/09/2001 2 : 1
W
Liverpool A
Anfield
13/10/2001 1 : 1
D
Chelsea H
Elland Road
21/10/2001 0 : 0
D
Manchester United A
Old Trafford
27/10/2001 1 : 1
D
Tottenham Hotspur H
Elland Road
04/11/2001 2 : 1
W
Sunderland A
Stadium Of Light
18/11/2001 0 : 2
L
Aston Villa H
Elland Road
25/11/2001 1 : 1
D
Fulham A
Craven Cottage
02/12/2001 0 : 0
D
Blackburn Rovers A
Ewood Park
09/12/2001 2 : 1
W
Leicester City H
Elland Road
16/12/2001 2 : 2
D
Everton H
Elland Road
19/12/2001 3 : 2
W
Newcastle United H
Elland Road
22/12/2001 3 : 4
L
Bolton Wanderers A
Reebok Stadium
26/12/2001 3 : 0
W
Southampton A
St Marys Stadium
29/12/2001 1 : 0
W
West Ham United H
Elland Road
01/01/2002 3 : 0
W
Newcastle United A
St James Park
12/01/2002 1 : 3
L
Arsenal H
Elland Road
20/01/2002 1 : 1
D
Chelsea A
Stamford Bridge
30/01/2002 0 : 2
L
Liverpool H
Elland Road
03/02/2002 0 : 4
L
Middlesbrough A
Riverside Stadium
09/02/2002 2 : 2
D
Charlton Athletic H
Elland Road
24/02/2002 0 : 0
D
Everton A
Goodison Park
03/03/2002 0 : 0
D
Ipswich Town H
Elland Road
06/03/2002 2 : 0
W
Blackburn Rovers H
Elland Road
17/03/2002 3 : 1
W
Leicester City A
Filbert Street
23/03/2002 2 : 0
W
Manchester United H
Elland Road
30/03/2002 3 : 4
L
Tottenham Hotspur A
White Hart Lane
01/04/2002 1 : 2
L
Sunderland H
Elland Road
07/04/2002 2 : 0
W
Aston Villa A
Villa Park
13/04/2002 1 : 0
W
Fulham H
Elland Road
20/04/2002 0 : 1
L
Derby County A
Pride Park
27/04/2002 1 : 0
W
Middlesbrough H
Elland Road
11/05/2002 1 : 0
W
FA Cup
Venue
Date Score
Rushden & Diamonds
FA Cup 3rd Round
A
Nene Park
02/01/1999 0 : 0
D
Rushden & Diamonds
FA Cup 3rd Round Replay
H
Elland Road
13/01/1999 3 : 1
W
Portsmouth
FA Cup 4th Round
A
Fratton Park
23/01/1999 5 : 1
W
Tottenham Hotspur
FA Cup 5th Round
H
Elland Road
13/02/1999 1 : 1
D
Tottenham Hotspur
FA Cup 5th Round Replay
A
White Hart Lane
24/02/1999 0 : 2
L
Port Vale
FA Cup 3rd Round
H
Elland Road
12/12/1999 2 : 0
W
Manchester City
FA Cup 4th Round
A
Maine Road
09/01/2000 5 : 2
W
Aston Villa
FA Cup 5th Round
A
Villa Park
30/01/2000 2 : 3
L
Barnsley
FA Cup 3rd Round
H
Elland Road
06/01/2001 1 : 0
W
Liverpool
FA Cup 4th Round
H
Elland Road
27/01/2001 0 : 2
L
Cardiff City
FA Cup 3rd Round
A
Ninian Park
06/01/2002 1 : 2
L
League Cup
Venue
Date Score
Bradford City
Worthington Cup 3rd Round
H
Elland Road
28/10/1998 1 : 0
W
Leicester City
Worthington Cup 4th Round
A
Filbert Street
11/11/1998 1 : 2
L
Blackburn Rovers
Worthington Cup 3rd Round
H
Elland Road
13/10/1999 1 : 0
W
Leicester City
Worthington Cup 4th Round
A
Filbert Street
15/12/1999 0 : 0
(2 : 4 p)
D
Tranmere Rovers
Worthington Cup 3rd Round
A
Prenton Park
31/10/2000 2 : 3
L
Leicester City
Worthington Cup 3rd Round
A
Filbert Street
09/10/2001 6 : 0
W
Chelsea
Worthington Cup 4th Round
H
Elland Road
28/11/2001 0 : 2
L
Europe
Venue
Date Score
Roma
UEFA Cup 2nd Round 1st Leg
A
Olympic Stadium
20/10/1998 0 : 1
L
Roma
UEFA Cup 2nd Round 2nd Leg
H
Elland Road
03/11/1998 0 : 0
D
Partizan Belgrade
UEFA Cup 1st Round 1st Leg
A
Abe Lenstra Stadium
14/09/1999 3 : 1
W
Partizan Belgrade
UEFA Cup 1st Round 2nd Leg
H
Elland Road
30/09/1999 1 : 0
W
Lokomotiv Moscow
UEFA Cup 2nd Round 1st Leg
H
Elland Road
21/10/1999 4 : 1
W
Lokomotiv Moscow
UEFA Cup 2nd Round 2nd Leg
A
Lokomotiv Stadium
04/11/1999 3 : 0
W
Spartak Moscow
UEFA Cup 3rd Round 1st Leg
A
The Georgi Asparuchov Stadium
02/12/1999 1 : 2
L
Spartak Moscow
UEFA Cup 3rd Round 2nd Leg
H
Elland Road
09/12/1999 1 : 0
W
Roma
UEFA Cup 4th Round 1st Leg
A
Olympic Stadium
02/03/2000 0 : 0
D
Roma
UEFA Cup 4th Round 2nd Leg
H
Elland Road
09/03/2000 1 : 0
W
Slavia Prague
UEFA Cup Quarter Final 1st Leg
H
Elland Road
16/03/2000 3 : 0
W
Slavia Prague
UEFA Cup Quarter Final 2nd Leg
A
Strahov Stadium
26/03/2000 1 : 2
L
Galatasaray
UEFA Cup Semi Final 1st Leg
A
Ali Semi Yen
06/04/2000 0 : 2
L
Galatasaray
UEFA Cup Semi Final 2nd Leg
H
Elland Road
20/04/2000 2 : 2
D
1860 Munich
Champions League 3rd Qualifying Round 1st Leg
H
Elland Road
09/08/2000 2 : 1
W
1860 Munich
Champions League 3rd Qualifying Round 2nd Leg
A
Olympic Stadium
23/08/2000 1 : 0
W
Barcelona
Champions Leaguue Phase 1 Group H
A
Nou Camp
13/09/2000 0 : 4
L
AC Milan
Champions League Phase 1 Group H
H
Elland Road
19/09/2000 1 : 0
W
Besiktas
Champions League Phase 1 Group H
H
Elland Road
26/09/2000 6 : 0
W
Besiktas
Champions League Phase 1 Group H
A
Inonu Stadium
18/10/2000 0 : 0
D
Barcelona
Champions League Phase 1 Group H
H
Elland Road
24/10/2000 1 : 1
D
AC Milan
Champions League Phase 1 Group H
A
San Siro
08/11/2000 1 : 1
D
Real Madrid
Champions League Phase 2 Group D
H
Elland Road
22/11/2000 0 : 2
L
Lazio
Champions League Phase 2 Group D
A
Olympic Stadium
05/12/2000 1 : 0
W
Anderlecht
Champions League Phase 2 Group D
H
Elland Road
13/02/2001 2 : 1
W
Anderlecht
Champions League Phase 2 Group D
A
Vanden Stock Stadium
21/02/2001 4 : 1
W
Real Madrid
Champions League Phase 2 Group D
A
Santiago Bernabeu
06/03/2001 2 : 3
L
Lazio
Champions League Phase 2 Group D
H
Elland Road
14/03/2001 3 : 3
D
Deportivo La Coruna
Champions League Quarter Final 1st Leg
H
Elland Road
04/04/2001 3 : 0
W
Deportivo La Coruna
Champions League Quarter Final 2nd Leg
A
Riazor
17/04/2001 0 : 2
L
Valencia
Champions League Semi Final 1st Leg
H
Elland Road
02/05/2001 0 : 0
D
Valencia
Champions League Semi Final 2nd Leg
A
Mestalla
08/05/2001 0 : 3
L
Maritimo
UEFA Cup 1st Round 1st Leg
A
Estadio Dos Barreiros
20/09/2001 0 : 1
L
Maritimo
UEFA Cup 1st Round 2nd Leg
H
Elland Road
27/09/2001 3 : 0
W
Troyes
UEFA Cup 2nd Round 1st Leg
H
Elland Road
18/10/2001 4 : 2
W
Troyes
UEFA Cup 2nd Round 2nd Leg
A
Stade De L’Aube
01/11/2001 2 : 3
L
Grasshoppers
UEFA Cup 3rd Round 1st Leg
A
Hardtrum Stadium
22/11/2001 2 : 1
W
Grasshoppers
UEFA Cup 3rd Round 2nd Leg
H
Elland Road
06/12/2001 2 : 2
D
PSV Eindhoven
UEFA Cup 4th Round 1st Leg
A
Phillips Stadion
21/02/2002 0 : 0
D
PSV Eindhoven
UEFA Cup 4th Round 2nd Leg
H
Elland Road
28/02/2002 0 : 1
L


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