Every competitive match Liverpool played in 1999–00, in Premier League — 43 matches, 22 won, 10 drawn, 11 lost, with scorers and attendances where the record holds them.
| Date | Competition | Venue | Opponent | Their season | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 7 Aug 1999 | Premier League | A | Sheffield Wednesday | Sheffield Wednesday 1999–00 | 2–1 | Robbie Fowler 75, Titi Camara 84 | 34,853 |
| 14 Aug 1999 | Premier League | H | Watford | Watford 1999–00 | 0–1 | 44,174 | |
| 21 Aug 1999 | Premier League | A | Middlesbrough | Middlesbrough 1999–00 | 0–1 | 34,783 | |
| 23 Aug 1999 | Premier League | A | Leeds United | Leeds United 1999–00 | 2–1 | Titi Camara 45, Lucas Radebe 55 | 39,703 |
| 28 Aug 1999 | Premier League | H | Arsenal | Arsenal 1999–00 | 2–0 | Robbie Fowler 8, Patrik Berger 76 | 44,886 |
| 11 Sep 1999 | Premier League | H | Manchester United | Manchester United 1999–00 | 2–3 | Sami Hyypiä 23, Patrik Berger 69 | 44,929 |
| 14 Sep 1999 | League Cup | A | Hull City | Hull City 1999–00 | 5–1 | Danny Murphy 10, Danny Murphy 30, Erik Meijer 48, Erik Meijer 75, Steve Staunton 89 | 10,034 |
| 18 Sep 1999 | Premier League | A | Leicester City | Leicester City 1999–00 | 2–2 | Michael Owen 23, Michael Owen 39 | 21,623 |
| 21 Sep 1999 | League Cup | H | Hull City | Hull City 1999–00 | 4–2 | Danny Murphy 33, Leyton Maxwell 46, Karl-Heinz Riedle 65, Karl-Heinz Riedle 89 | 24,318 |
| 27 Sep 1999 | Premier League | H | Everton | Everton 1999–00 | 0–1 | 44,802 | |
| 2 Oct 1999 | Premier League | A | Aston Villa | Aston Villa 1999–00 | 0–0 | 39,217 | |
| 13 Oct 1999 | League Cup | A | Southampton | Southampton 1999–00 | 1–2 | Michael Owen 53 | 13,822 |
| 16 Oct 1999 | Premier League | H | Chelsea | Chelsea 1999–00 | 1–0 | David Thompson 47 | 44,826 |
| 23 Oct 1999 | Premier League | A | Southampton | Southampton 1999–00 | 1–1 | Titi Camara 81 | 15,241 |
| 27 Oct 1999 | Premier League | H | West Ham United | West Ham United 1999–00 | 1–0 | Titi Camara 43 | 44,012 |
| 1 Nov 1999 | Premier League | H | Bradford City | Bradford City 1999–00 | 3–1 | Titi Camara 20, Jamie Redknapp 41, Vegard Heggem 80 | 40,483 |
| 6 Nov 1999 | Premier League | H | Derby County | Derby County 1999–00 | 2–0 | Danny Murphy 65, Jamie Redknapp 69 | 44,467 |
| 20 Nov 1999 | Premier League | A | Sunderland | Sunderland 1999–00 | 2–0 | Michael Owen 63, Patrik Berger 85 | 42,015 |
| 27 Nov 1999 | Premier League | A | West Ham United | West Ham United 1999–00 | 0–1 | 26,043 | |
| 5 Dec 1999 | Premier League | H | Sheffield Wednesday | Sheffield Wednesday 1999–00 | 4–1 | Sami Hyypiä 21, Danny Murphy 41, Steven Gerrard 69, David Thompson 78 | 42,517 |
| 12 Dec 1999 | FA Cup | A | Huddersfield Town | Huddersfield Town 1999–00 | 2–0 | Titi Camara 36, Dominic Matteo 59 | 23,678 |
| 18 Dec 1999 | Premier League | H | Coventry City | Coventry City 1999–00 | 2–0 | Michael Owen 45, Titi Camara 74 | 44,024 |
| 26 Dec 1999 | Premier League | A | Newcastle United | Newcastle United 1999–00 | 2–2 | Michael Owen 29, Michael Owen 45 | 36,445 |
| 28 Dec 1999 | Premier League | H | Wimbledon | Wimbledon 1999–00 | 3–1 | Michael Owen 58, Patrik Berger 68, Robbie Fowler 80 | 44,107 |
| 3 Jan 2000 | Premier League | A | Tottenham Hotspur | Tottenham Hotspur 1999–00 | 0–1 | 36,044 | |
| 10 Jan 2000 | FA Cup | H | Blackburn Rovers | Blackburn Rovers 1999–00 | 0–1 | 32,839 | |
| 15 Jan 2000 | Premier League | A | Watford | Watford 1999–00 | 3–2 | Patrik Berger 10, David Thompson 41, Vladimír Šmicer 71 | 21,367 |
| 22 Jan 2000 | Premier League | H | Middlesbrough | Middlesbrough 1999–00 | 0–0 | 44,324 | |
| 5 Feb 2000 | Premier League | H | Leeds United | Leeds United 1999–00 | 3–1 | Dietmar Hamann 20, Patrik Berger 69, Danny Murphy 90 | 44,793 |
| 13 Feb 2000 | Premier League | A | Arsenal | Arsenal 1999–00 | 1–0 | Titi Camara 18 | 38,098 |
| 4 Mar 2000 | Premier League | A | Manchester United | Manchester United 1999–00 | 1–1 | Patrik Berger 28 | 61,592 |
| 11 Mar 2000 | Premier League | H | Sunderland | Sunderland 1999–00 | 1–1 | Patrik Berger 2 | 44,693 |
| 15 Mar 2000 | Premier League | H | Aston Villa | Aston Villa 1999–00 | 0–0 | 43,615 | |
| 18 Mar 2000 | Premier League | A | Derby County | Derby County 1999–00 | 2–0 | Michael Owen 17, Titi Camara 86 | 33,378 |
| 25 Mar 2000 | Premier League | H | Newcastle United | Newcastle United 1999–00 | 2–1 | Titi Camara 51, Jamie Redknapp 88 | 44,743 |
| 1 Apr 2000 | Premier League | A | Coventry City | Coventry City 1999–00 | 3–0 | Michael Owen 23, Michael Owen 38, Emile Heskey 78 | 23,098 |
| 9 Apr 2000 | Premier League | H | Tottenham Hotspur | Tottenham Hotspur 1999–00 | 2–0 | Patrik Berger 34, Michael Owen 61 | 44,536 |
| 16 Apr 2000 | Premier League | A | Wimbledon | Wimbledon 1999–00 | 2–1 | Emile Heskey 37, Emile Heskey 62 | 26,102 |
| 21 Apr 2000 | Premier League | A | Everton | Everton 1999–00 | 0–0 | 40,052 | |
| 29 Apr 2000 | Premier League | A | Chelsea | Chelsea 1999–00 | 0–2 | 34,957 | |
| 3 May 2000 | Premier League | H | Leicester City | Leicester City 1999–00 | 0–2 | 43,456 | |
| 7 May 2000 | Premier League | H | Southampton | Southampton 1999–00 | 0–0 | 44,015 | |
| 14 May 2000 | Premier League | A | Bradford City | Bradford City 1999–00 | 0–1 | 18,276 |
63 of the goals in this season carry a named scorer.
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