Every competitive match Chelsea played in 1999–00, in Premier League — 61 matches, 32 won, 15 drawn, 14 lost, with scorers and attendances where the record holds them.
| Date | Competition | Venue | Opponent | Their season | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 7 Aug 1999 | Premier League | H | Sunderland | Sunderland 1999–00 | 4–0 | Gustavo Poyet 20, Gianfranco Zola 32, Gustavo Poyet 56, Tore André Flo 77 | |
| 12 Aug 1999 | Champions League | H | Skonto | 3–0 | Celestine Babayaro 76, Gustavo Poyet 77, Chris Sutton 84 | ||
| 14 Aug 1999 | Premier League | A | Leicester City | Leicester City 1999–00 | 2–2 | Dennis Wise 48, Frank Sinclair 90+3 | |
| 21 Aug 1999 | Premier League | H | Aston Villa | Aston Villa 1999–00 | 1–0 | Ugo Ehiogu 52 | |
| 25 Aug 1999 | Champions League | A | Skonto | 0–0 | |||
| 28 Aug 1999 | Premier League | A | Wimbledon | Wimbledon 1999–00 | 1–0 | Dan Petrescu 78 | |
| 11 Sep 1999 | Premier League | H | Newcastle United | Newcastle United 1999–00 | 1–0 | Franck Leboeuf 37 | |
| 15 Sep 1999 | Champions League | H | A.C. Milan | 0–0 | 33,873 | ||
| 18 Sep 1999 | Premier League | A | Watford | Watford 1999–00 | 0–1 | ||
| 21 Sep 1999 | Champions League | A | Hertha BSC | 1–2 | Franck Leboeuf 86 | 51,541 | |
| 25 Sep 1999 | Premier League | A | Middlesbrough | Middlesbrough 1999–00 | 1–0 | Bernard Lambourde 54 | |
| 29 Sep 1999 | Champions League | H | Galatasaray S.K. | 1–0 | Dan Petrescu 55 | 33,426 | |
| 3 Oct 1999 | Premier League | H | Manchester United | Manchester United 1999–00 | 5–0 | Gustavo Poyet 1, Chris Sutton 16, Gustavo Poyet 55, Henning Berg 58, Jody Morris 82 | |
| 13 Oct 1999 | League Cup | H | Huddersfield Town | Huddersfield Town 1999–00 | 0–1 | 21,008 | |
| 16 Oct 1999 | Premier League | A | Liverpool | Liverpool 1999–00 | 0–1 | ||
| 19 Oct 1999 | Champions League | A | Galatasaray S.K. | 5–0 | Tore André Flo 32, Tore André Flo 49, Gianfranco Zola 54, Gabriele Ambrosetti 87, Dennis Wise | 20,600 | |
| 23 Oct 1999 | Premier League | H | Arsenal | Arsenal 1999–00 | 2–3 | Tore André Flo 38, Dan Petrescu 52 | |
| 26 Oct 1999 | Champions League | A | A.C. Milan | 1–1 | Dennis Wise 77 | 74,855 | |
| 30 Oct 1999 | Premier League | A | Derby County | Derby County 1999–00 | 1–3 | Franck Leboeuf 10 | |
| 4 Nov 1999 | Champions League | H | Hertha BSC | 2–0 | Didier Deschamps 11, Albert Ferrer 44 | 33,623 | |
| 7 Nov 1999 | Premier League | H | West Ham United | West Ham United 1999–00 | 0–0 | ||
| 20 Nov 1999 | Premier League | A | Everton | Everton 1999–00 | 1–1 | Tore André Flo 90 | |
| 24 Nov 1999 | Champions League | H | Feyenoord | 3–1 | Celestine Babayaro 45, Tore André Flo 67, Tore André Flo 85 | 29,704 | |
| 28 Nov 1999 | Premier League | H | Bradford City | Bradford City 1999–00 | 1–0 | Tore André Flo 15 | |
| 4 Dec 1999 | Premier League | A | Sunderland | Sunderland 1999–00 | 1–4 | Gustavo Poyet 81 | |
| 7 Dec 1999 | Champions League | A | S.S. Lazio | 0–0 | 38,662 | ||
| 11 Dec 1999 | FA Cup | A | Hull City | Hull City 1999–00 | 6–1 | Gustavo Poyet, Gustavo Poyet, Gustavo Poyet, Chris Sutton, Roberto Di Matteo, Dennis Wise | 10,279 |
| 19 Dec 1999 | Premier League | H | Leeds United | Leeds United 1999–00 | 0–2 | ||
| 26 Dec 1999 | Premier League | A | Southampton | Southampton 1999–00 | 2–1 | Tore André Flo 18, Tore André Flo 43 | |
| 29 Dec 1999 | Premier League | H | Sheffield Wednesday | Sheffield Wednesday 1999–00 | 3–0 | Dennis Wise 31, Tore André Flo 35, Jody Morris 84 | |
| 4 Jan 2000 | Premier League | A | Coventry City | Coventry City 1999–00 | 2–2 | Tore André Flo 55, Tore André Flo 83 | |
| 8 Jan 2000 | Premier League | A | Bradford City | Bradford City 1999–00 | 1–1 | Dan Petrescu 58 | |
| 12 Jan 2000 | Premier League | H | Tottenham Hotspur | Tottenham Hotspur 1999–00 | 1–0 | George Weah 86 | |
| 15 Jan 2000 | Premier League | H | Leicester City | Leicester City 1999–00 | 1–1 | Dennis Wise 85 | |
| 19 Jan 2000 | FA Cup | H | Nottingham Forest | Nottingham Forest 1999–00 | 2–0 | Frank Leboeuf, Dennis Wise | 30,125 |
| 22 Jan 2000 | Premier League | A | Aston Villa | Aston Villa 1999–00 | 0–0 | ||
| 31 Jan 2000 | FA Cup | H | Leicester City | Leicester City 1999–00 | 2–1 | Gustavo Poyet, George Weah | 30,141 |
| 5 Feb 2000 | Premier League | A | Tottenham Hotspur | Tottenham Hotspur 1999–00 | 1–0 | Bernard Lambourde 52 | |
| 12 Feb 2000 | Premier League | H | Wimbledon | Wimbledon 1999–00 | 3–1 | Gustavo Poyet 79, George Weah 80, Jody Morris 90 | |
| 20 Feb 2000 | FA Cup | H | Gillingham | Gillingham 1999–00 | 5–0 | Tore André Flo, John Terry, George Weah, Gianfranco Zola, Jody Morris | 34,205 |
| 26 Feb 2000 | Premier League | H | Watford | Watford 1999–00 | 2–1 | Marcel Desailly 2, Jon Harley 65 | |
| 29 Feb 2000 | Champions League | A | Olympique de Marseille | 0–1 | 24,700 | ||
| 4 Mar 2000 | Premier League | A | Newcastle United | Newcastle United 1999–00 | 1–0 | Gustavo Poyet 22 | |
| 8 Mar 2000 | Champions League | H | Olympique de Marseille | 1–0 | Dennis Wise 27 | 33,206 | |
| 11 Mar 2000 | Premier League | H | Everton | Everton 1999–00 | 1–1 | Dennis Wise 29 | |
| 14 Mar 2000 | Champions League | A | Feyenoord | 3–1 | Gianfranco Zola 39, Dennis Wise 64, Tore André Flo 69 | 44,000 | |
| 18 Mar 2000 | Premier League | A | West Ham United | West Ham United 1999–00 | 0–0 | ||
| 22 Mar 2000 | Champions League | H | S.S. Lazio | 1–2 | Gustavo Poyet 44 | 34,260 | |
| 25 Mar 2000 | Premier League | H | Southampton | Southampton 1999–00 | 1–1 | Dean Richards 75 | |
| 1 Apr 2000 | Premier League | A | Leeds United | Leeds United 1999–00 | 1–0 | Jon Harley 62 | |
| 5 Apr 2000 | Champions League | H | Barcelona | 3–1 | Gianfranco Zola 30, Tore André Flo 34, Tore André Flo 38 | 34,000 | |
| 9 Apr 2000 | FA Cup | N | Newcastle United | Newcastle United 1999–00 | 2–1 | Gustavo Poyet, Gustavo Poyet | 73,876 |
| 12 Apr 2000 | Premier League | H | Coventry City | Coventry City 1999–00 | 2–1 | Colin Hendry 53, Gianfranco Zola 56 | |
| 15 Apr 2000 | Premier League | A | Sheffield Wednesday | Sheffield Wednesday 1999–00 | 0–1 | ||
| 18 Apr 2000 | Champions League | A | Barcelona | 1–5 | Tore André Flo 60 | 80,000 | |
| 22 Apr 2000 | Premier League | H | Middlesbrough | Middlesbrough 1999–00 | 1–1 | Gustavo Poyet 10 | |
| 24 Apr 2000 | Premier League | A | Manchester United | Manchester United 1999–00 | 2–3 | Dan Petrescu 22, Gianfranco Zola 36 | |
| 29 Apr 2000 | Premier League | H | Liverpool | Liverpool 1999–00 | 2–0 | George Weah 2, Roberto Di Matteo 14 | |
| 6 May 2000 | Premier League | A | Arsenal | Arsenal 1999–00 | 1–2 | Gustavo Poyet 79 | |
| 14 May 2000 | Premier League | H | Derby County | Derby County 1999–00 | 4–0 | Gianfranco Zola 46, Gustavo Poyet 55, Roberto Di Matteo 69, Tore André Flo 90 | |
| 20 May 2000 | FA Cup | N | Aston Villa | Aston Villa 1999–00 | 1–0 | Roberto Di Matteo | 78,217 |
96 of the goals in this season carry a named scorer.
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