1999–2000 Leeds United A.F.C. season

After a promising previous season, good times looked to be on the horizon for David O'Leary and his young team in his first full season in charge, even after losing their previous season's top scorer Jimmy Floyd Hasselbaink to Spanish side Atletico Madrid. O'Leary added more young quality to his squad, defenders Michael Duberry and Danny Mills were signed from Chelsea and Charlton respectively. Midfielders Eirik Bakke and Jason Wilcox also joined, along with striker Michael Bridges.

Leeds had a tough start in the league, wins over Southampton and newly promoted Sunderland were each followed with losses to Liverpool and Manchester United, but a 2–1 win at Tottenham saw Leeds begin a record of 10 straight wins at home. Leeds stormed to the top of the Premiership, with new striker Michael Bridges and Harry Kewell scoring regularly, but in the New Year star players Lee Bowyer and Jonathan Woodgate were involved in an off the pitch incident in Leeds city centre, a saga which was to hamper the club for the next few years. In the meantime, Leeds made relatively early exits from both domestic cup competitions, going out of the League Cup to eventual winners Leicester City, and the FA Cup to eventual runners-up Aston Villa.

Defeats to Manchester United and Liverpool saw Leeds lose ground in the title race; however, Leeds were progressing well in the UEFA Cup and reached the semi-final against Turkish side Galatasaray. However two Leeds supporters were stabbed to death in clashes before the game; the deaths clearly affected Leeds on the pitch that night, and they lost the first leg of the tie 2–0. A 2–2 draw in the return leg meant Leeds were knocked out of the UEFA Cup.

Domestically, four consecutive league defeats almost ended hopes of finishing in the top three, but Leeds recovered well enough to go into the final day in third place, leaving them needing to better Liverpool's result in order to secure Champions League football. While Leeds could only draw, their neighbours Bradford City did them a huge favour by unexpectedly defeating Liverpool, securing not only their own top-flight survival, but third place for Leeds. Champions League qualification capped off an overall successful season for Leeds, and seemingly provided a platform for the club to build on going forwards.

Results summary

Results by round

Squad at end of season[1]

Note: Flags indicate national team as defined under FIFA eligibility rules. Players may hold more than one non-FIFA nationality.

No. Pos. Nation Player 1 GK  ENG Nigel Martyn 2 DF  IRL Gary Kelly 3 DF  IRL Ian Harte 4 DF  NOR Alfie Haaland 5 DF  RSA Lucas Radebe 6 DF  ENG Jonathan Woodgate 7 MF  SCO David Hopkin 8 FW  ENG Michael Bridges 10 FW  AUS Harry Kewell 11 MF  ENG Lee Bowyer 12 FW  ENG Darren Huckerby

No. Pos. Nation Player 13 GK  ENG Paul Robinson 14 MF  IRL Stephen McPhail[lower-alpha 3] 16 MF  ENG Jason Wilcox 17 FW  ENG Alan Smith 18 DF  ENG Danny Mills 19 MF  NOR Eirik Bakke 20 MF  WAL Matt Jones 21 DF  AUT Martin Hiden 22 DF  ENG Michael Duberry 23 MF  ENG David Batty

Left club during season

Note: Flags indicate national team as defined under FIFA eligibility rules. Players may hold more than one non-FIFA nationality.

No. Pos. Nation Player 15 MF  POR Bruno Ribeiro (to Sheffield United) 16 DF  ENG Danny Granville (to Manchester City) 28 DF  ENG Paul Shepherd (to Ayr United)

No. Pos. Nation Player 29 MF  ENG Mark Jackson (to Scunthorpe United) 31 MF  NOR Tommy Knarvik (to Brann)

The following players did not appear for the first team this season.

Note: Flags indicate national team as defined under FIFA eligibility rules. Players may hold more than one non-FIFA nationality.

No. Pos. Nation Player 24 DF  NZL Danny Hay 25 DF  SCO David Robertson 26 GK  AUS Danny Milosevic 27 DF  IRL Alan Maybury 30 DF  NED Robert Molenaar 32 FW  ENG Neil Ross 33 MF  NIR Wesley Boyle 34 MF  ENG Kevin Dixon 35 FW  ENG Lee Matthews 36 GK  ENG Shaun Allaway 37 FW  ENG Tony Hackworth 38 DF  IRL Damian Lynch 39 DF  ENG Gareth Evans 40 MF  NIR Simon Watson 41 MF  NIR Brian Lagen

No. Pos. Nation Player 42 DF  WAL Kevin Evans 43 FW  NIR Warren Feeney — DF  ENG Jason Lanns — DF  ENG Frazer Richardson — DF  IRL Alan Martin — DF  AUS Shane Cansdell-Sherriff — MF  ENG Jamie McMaster — MF  ENG Harpal Singh — FW  ENG Craig Farrell — FW  ENG Caleb Folan

(Starting appearances + substitute appearances)[2]

No.	Pos.	Name	League		FA Cup		League Cup		UEFA Cup		Total		Discipline
			Apps	Goals	Apps	Goals	Apps	Goals	Apps	Goals	Apps	Goals
1	GK	Nigel Martyn	38	0	3	0	2	0	12	0	55	0	2	0
2	DF	Gary Kelly	28+3	0	3	0	2	0	11	0	44+3	0	7	0
3	DF	Ian Harte	33	6	3	1	1	0	12	1	49	8	11	1
4	MF	Alfie Haaland	7+6	0	0	0	0	0	5+1	1	12+7	0	5	0
5	DF	Lucas Radebe	31	0	2	0	2	0	11	2	46	2	6	1
6	DF	Jonathan Woodgate	32+2	1	3	0	2	0	10	0	47+2	1	1	0
7	MF	David Hopkin	10+4	1	0	0	1	0	2+1	0	13+5	1	1	0
8	FW	Michael Bridges	32+2	19	1+1	0	2	0	12	2	47+3	21	9	0
10	FW	Harry Kewell	36	10	3	2	2	0	12	5	53	17	7	1
11	MF	Lee Bowyer	31+2	5	3	1	1	0	11	5	46+2	11	19	0
12	FW	Darren Huckerby	9+24	2	3	0	0+1	0	1+8	1	11+35	3	0	0
14	MF	Stephen McPhail	23+1	2	0	0	1+1	0	9	0	36+2	2	0	0
16	MF	Jason Wilcox	15+5	3	2	0	0	0	3+1	1	20+6	4	3	0
17	FW	Alan Smith	20+6	4	2+1	1	1	0	2+6	1	25+13	6	10	1
18	DF	Danny Mills	16+1	1	0+1	0	1	1	2	0	19+2	2	5	0
19	MF	Eirik Bakke	24+5	2	3	4	2	0	9+1	2	38+6	8	7	0
20	MF	Matt Jones	5+6	0	0+1	0	0+1	0	3+2	0	8+10	0	3	0
21	DF	Martin Hiden	0+1	0	0	0	0	0	0	0	0+1	0	0	0
22	DF	Michael Duberry	12+1	1	1	0	0+1	0	1	0	14+2	1	4	1
23	MF	David Batty	16	0	0	0	2	0	4	0	22	0	4	0