The 1999–2000 season was Chelsea F.C.'s 86th competitive season, eighth consecutive season in the FA Premier League and 94th year as a club.

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Chelsea

1999–2000 season
Chairman	Ken Bates
Manager	Gianluca Vialli
Premier League	5th
FA Cup	Winners
League Cup	Third round
UEFA Champions League	Quarter-finals
Top goalscorer	League: Tore André Flo Gus Poyet (10) All: Tore André Flo (19)
Highest home attendance	35,113 (vs. Everton, 11 May 2000)
Lowest home attendance	21,008 (vs. Huddersfield Town, 13 October 1999)
Home colours Away colours Third colours
← 1998–99 2000–01 →

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After a very good third-place finish last season, Chelsea qualified for the Champions League third qualifying round, and were expected to go one better and win the title. France captain Didier Deschamps was signed for £3 million from Juventus to add even more quality and experience to a Chelsea midfield that already boasted Dennis Wise, Roberto Di Matteo and Gustavo Poyet. Blackburn Rovers striker Chris Sutton was also signed for £10 million, but he proved to be a flop with only one league goal all season, which came in a 5-0 drubbing of Man Utd at Stamford Bridge. His strike partner, Gianfranco Zola, had a poor league season by his standard, scoring just four goals, but he made up for that by again setting up many more goals for the team. Chelsea opened the season with 4–0 win over newly promoted Sunderland with Gus Poyet scoring a stunning scissors kick goal. Zola, in contrast to his average league form, made Europe sit up and notice as he led Chelsea's Champions league debut appearance in the group stage. Chelsea were drawn against AC Milan, Hertha Berlin and Galatasary with their first game being against AC Milan at Stamford Bridge. Chelsea topped Group H with 11 points after some standout performances, particularly an impressive 5–0 win in Turkey and two creditable draws home and away with AC Milan.

Zola scored a spectacular free kick in a 3–1 win over F.C. Barcelona at Stamford Bridge, but Chelsea were eliminated in the second leg at the Nou Camp. On the Premier league front, Gianluca Vialli's side finished a solid fifth place in the final table but were too inconsistent to mount anything like a title challenge. Chelsea won their fourth cup in four seasons with a 1–0 win over Aston Villa at Wembley, after David James dropped the ball from a Chelsea corner allowing Di Matteo to score. Chelsea had the last cup final triumph at the old Wembley stadium before it was rebuilt.^[1] Gus Poyet was key during Chelsea's FA cup run, scoring a hat trick against Hull at Boothferry Park in a 6–1 win and netting twice against Newcastle at Wembley.

On 26 December 1999, in their 1–2 away win over Southampton, Chelsea became the first team in the Football League history to field a starting eleven without an English player. The squad was made up of: Ed de Goey, Albert Ferrer, Franck Leboeuf, Emerson Thome, Celestine Babayaro, Deschamps, Dan Petrescu, Di Matteo, Poyet, Gabriele Ambrosetti and Tore André Flo.

Results summary

Results by round

Squad at end of season^[2]

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

More information No., Pos. ...

No. Pos. Nation Player 1 GK  NED Ed de Goey 2 DF  ROU Dan Petrescu 3 DF  NGA Celestine Babayaro 4 DF  DEN Jes Høgh 5 DF  FRA Frank Leboeuf 6 DF  FRA Marcel Desailly 7 MF  FRA Didier Deschamps 8 MF  URU Gustavo Poyet 9 FW  ENG Chris Sutton 11 MF  ENG Dennis Wise (captain) 13 GK  ENG Kevin Hitchcock 14 DF  ENG Graeme Le Saux 15 DF  NED Mario Melchiot 16 MF  ITA Roberto Di Matteo 17 DF  ESP Albert Ferrer

No. Pos. Nation Player 18 MF  ITA Gabriele Ambrosetti 19 FW  NOR Tore Andre Flo 20 MF  ENG Jody Morris 21 DF  FRA Bernard Lambourde 22 FW  ENG Mark Nicholls 24 MF  ITA Samuele Dalla Bona 25 FW  ITA Gianfranco Zola 26 DF  ENG John Terry 28 MF  ENG Rob Wolleaston 29 DF  ENG Neil Clement 30 DF  BRA Emerson Thome 31 FW  LBR George Weah (on loan from Milan) 32 FW  FIN Mikael Forssell 33 DF  ITA Luca Percassi 34 DF  ENG Jon Harley 36 FW  ENG Leon Knight

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Left club during season

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

More information No., Pos. ...

No. Pos. Nation Player 12 MF  DEN Bjarne Goldbæk (to Fulham)

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More information No., Pos ...

No.	Pos	Nat	Player	Total		FA Premier League		UEFA Champions League		FA Cup		Football League Cup
				Apps	Goals	Apps	Goals	Apps	Goals	Apps	Goals	Apps	Goals
1	GK	NED	Ed de Goey	59	0	37	0	16	0	6	0	0	0
2	DF	ROU	Dan Petrescu	47	5	24+5	4	13+2	1	2+1	0	0	0
3	DF	NGA	Celestine Babayaro	41	2	23+2	0	14+1	2	1	0	0	0
4	DF	DEN	Jes Høgh	17	0	6+3	0	2+3	0	2	0	1	0
5	DF	FRA	Frank Leboeuf	46	4	28	2	13+1	1	4	1	0	0
6	DF	FRA	Marcel Desailly	43	1	23	1	16	0	4	0	0	0
7	MF	FRA	Didier Deschamps	47	1	24+3	0	14	1	6	0	0	0
8	MF	URU	Gustavo Poyet	53	18	25+8	10	11+3	2	6	6	0	0
9	FW	ENG	Chris Sutton	39	3	21+7	1	3+4	1	3+1	1	0	0
11	MF	ENG	Dennis Wise	50	9	29+1	4	14+1	4	5	1	0	0
12	MF	DEN	Bjarne Goldbæk	9	0	2+4	0	1+1	0	0	0	1	0
14	DF	ENG	Graeme Le Saux	13	0	6+2	0	3+1	0	0	0	1	0
15	DF	NED	Mario Melchiot	6	0	4+1	0	0	0	1	0	0	0
16	MF	ITA	Roberto Di Matteo	31	4	14+4	2	3+6	0	3	2	1	0
17	DF	ESP	Albert Ferrer	41	1	24+1	0	14	1	2	0	0	0
18	MF	ITA	Gabriele Ambrosetti	23	1	9+7	0	1+4	1	0+1	0	1	0
19	FW	NOR	Tore André Flo	57	19	20+14	10	14+2	8	2+4	1	1	0
20	MF	ENG	Jody Morris	46	4	19+11	3	6+5	0	1+3	1	1	0
21	DF	FRA	Bernard Lambourde	21	2	12+3	2	0+2	0	3	0	1	0
22	FW	ENG	Mark Nicholls	2	0	0	0	0+1	0	0	0	0+1	0
24	MF	ITA	Samuele Dalla Bona	3	0	0+2	0	0+1	0	0	0	0	0
25	FW	ITA	Gianfranco Zola	53	8	25+8	4	15	3	4+1	1	0	0
26	DF	ENG	John Terry	9	1	2+2	0	0	0	2+2	1	1	0
28	MF	ENG	Rob Wolleaston	2	0	0+1	0	0	0	0	0	0+1	0
29	DF	ENG	Neil Clement	1	0	0	0	0	0	1	0	0	0
30	DF	BRA	Emerson Thome	21	0	18+2	0	1	0	0	0	0	0
31	FW	LBR	George Weah	15	5	9+2	3	0	0	4	2	0	0
32	FW	FIN	Mikael Forssell	2	0	0	0	1	0	0	0	1	0
33	DF	ITA	Luca Percassi	1	0	0	0	0	0	0+1	0	0	0
34	DF	ENG	Jon Harley	26	2	13+4	2	1+3	0	5	0	0	0

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Statistics taken from.^[3][4][5] Squad details and shirt numbers from ^[6] and.^[7]