Every competitive match Manchester United played in 1999–00 — 55 matches, 36 won, 10 drawn, 9 lost, with scorers and attendances where the record holds them.
| Date | Competition | Venue | Opponent | Their season | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 1 Aug 1999 | Charity Shield | H | Arsenal | Arsenal 1999–00 | 1–2 | ||
| 8 Aug 1999 | Premier League | A | Everton | Everton 1999–00 | 1–1 | Dwight Yorke 7 | 39,141 |
| 11 Aug 1999 | Premier League | H | Sheffield Wednesday | Sheffield Wednesday 1999–00 | 4–0 | Paul Scholes 9, Dwight Yorke 35, Andy Cole 54, Ole Gunnar Solskjær 84 | 54,941 |
| 14 Aug 1999 | Premier League | H | Leeds United | Leeds United 1999–00 | 2–0 | Dwight Yorke 77, Dwight Yorke 80 | 55,187 |
| 22 Aug 1999 | Premier League | A | Arsenal | Arsenal 1999–00 | 2–1 | Roy Keane 59, Roy Keane 88 | 38,147 |
| 25 Aug 1999 | Premier League | A | Coventry City | Coventry City 1999–00 | 2–1 | Paul Scholes 63, Dwight Yorke 75 | 22,024 |
| 27 Aug 1999 | UEFA Cup | H | S.S. Lazio | 0–1 | |||
| 30 Aug 1999 | Premier League | H | Newcastle United | Newcastle United 1999–00 | 5–1 | Andy Cole 14, Andy Cole 46, Andy Cole 65, Andy Cole 71, Ryan Giggs 81 | 55,190 |
| 11 Sep 1999 | Premier League | A | Liverpool | Liverpool 1999–00 | 3–2 | Jamie Carragher 4, Andy Cole 18, Jamie Carragher 45 | 44,929 |
| 14 Sep 1999 | Champions League | H | GNK Dinamo Zagreb | 0–0 | |||
| 18 Sep 1999 | Premier League | H | Wimbledon | Wimbledon 1999–00 | 1–1 | Jordi Cruyff 74 | 55,189 |
| 22 Sep 1999 | Champions League | A | SK Sturm Graz | 3–0 | |||
| 25 Sep 1999 | Premier League | H | Southampton | Southampton 1999–00 | 3–3 | Teddy Sheringham 34, Dwight Yorke 38, Dwight Yorke 64 | 55,249 |
| 29 Sep 1999 | Champions League | H | Olympique de Marseille | 2–1 | |||
| 3 Oct 1999 | Premier League | A | Chelsea | Chelsea 1999–00 | 0–5 | 34,909 | |
| 13 Oct 1999 | League Cup | A | Aston Villa | Aston Villa 1999–00 | 0–3 | ||
| 16 Oct 1999 | Premier League | H | Watford | Watford 1999–00 | 4–1 | Dwight Yorke 40, Andy Cole 42, Denis Irwin 45, Andy Cole 50 | 55,188 |
| 19 Oct 1999 | Champions League | A | Olympique de Marseille | 0–1 | |||
| 23 Oct 1999 | Premier League | A | Tottenham Hotspur | Tottenham Hotspur 1999–00 | 1–3 | Ryan Giggs 24 | 36,072 |
| 27 Oct 1999 | Champions League | A | GNK Dinamo Zagreb | 2–1 | |||
| 30 Oct 1999 | Premier League | H | Aston Villa | Aston Villa 1999–00 | 3–0 | Paul Scholes 30, Andy Cole 45, Roy Keane 65 | 55,211 |
| 2 Nov 1999 | Champions League | H | SK Sturm Graz | 2–1 | |||
| 6 Nov 1999 | Premier League | H | Leicester City | Leicester City 1999–00 | 2–0 | Andy Cole 30, Andy Cole 83 | 55,191 |
| 20 Nov 1999 | Premier League | A | Derby County | Derby County 1999–00 | 2–1 | Nicky Butt 53, Andy Cole 84 | 33,370 |
| 23 Nov 1999 | Champions League | A | ACF Fiorentina | 0–2 | |||
| 4 Dec 1999 | Premier League | H | Everton | Everton 1999–00 | 5–1 | Denis Irwin 27, Ole Gunnar Solskjær 29, Ole Gunnar Solskjær 43, Ole Gunnar Solskjær 52, Ole Gunnar Solskjær 58 | 55,193 |
| 8 Dec 1999 | Champions League | H | Valencia CF | 3–0 | |||
| 18 Dec 1999 | Premier League | A | West Ham United | West Ham United 1999–00 | 4–2 | Dwight Yorke 9, Ryan Giggs 13, Ryan Giggs 20, Dwight Yorke 63 | 26,037 |
| 26 Dec 1999 | Premier League | H | Bradford City | Bradford City 1999–00 | 4–0 | Quinton Fortune 75, Dwight Yorke 79, Andy Cole 88, Roy Keane 89 | 55,188 |
| 28 Dec 1999 | Premier League | A | Sunderland | Sunderland 1999–00 | 2–2 | Roy Keane 27, Nicky Butt 87 | 42,026 |
| 24 Jan 2000 | Premier League | H | Arsenal | Arsenal 1999–00 | 1–1 | Teddy Sheringham 74 | 58,293 |
| 29 Jan 2000 | Premier League | H | Middlesbrough | Middlesbrough 1999–00 | 1–0 | David Beckham 87 | 61,267 |
| 2 Feb 2000 | Premier League | A | Sheffield Wednesday | Sheffield Wednesday 1999–00 | 1–0 | Teddy Sheringham 74 | 39,640 |
| 5 Feb 2000 | Premier League | H | Coventry City | Coventry City 1999–00 | 3–2 | Andy Cole 40, Andy Cole 55, Paul Scholes 77 | 61,380 |
| 12 Feb 2000 | Premier League | A | Newcastle United | Newcastle United 1999–00 | 0–3 | 36,470 | |
| 20 Feb 2000 | Premier League | A | Leeds United | Leeds United 1999–00 | 1–0 | Andy Cole 52 | 40,160 |
| 26 Feb 2000 | Premier League | A | Wimbledon | Wimbledon 1999–00 | 2–2 | Jordi Cruyff 30, Andy Cole 80 | 26,129 |
| 1 Mar 2000 | Champions League | H | Girondins de Bordeaux | 2–0 | |||
| 4 Mar 2000 | Premier League | H | Liverpool | Liverpool 1999–00 | 1–1 | Ole Gunnar Solskjær 45 | 61,592 |
| 7 Mar 2000 | Champions League | A | Girondins de Bordeaux | 2–1 | |||
| 11 Mar 2000 | Premier League | H | Derby County | Derby County 1999–00 | 3–1 | Dwight Yorke 13, Dwight Yorke 70, Dwight Yorke 72 | 61,619 |
| 15 Mar 2000 | Champions League | H | ACF Fiorentina | 3–1 | |||
| 18 Mar 2000 | Premier League | A | Leicester City | Leicester City 1999–00 | 2–0 | David Beckham 33, Dwight Yorke 84 | 22,170 |
| 21 Mar 2000 | Champions League | A | Valencia CF | 0–0 | |||
| 25 Mar 2000 | Premier League | A | Bradford City | Bradford City 1999–00 | 4–0 | Dwight Yorke 38, Dwight Yorke 40, Paul Scholes 71, David Beckham 79 | 18,276 |
| 1 Apr 2000 | Premier League | H | West Ham United | West Ham United 1999–00 | 7–1 | Paul Scholes 24, Denis Irwin 27, Andy Cole 45, Paul Scholes 51, Paul Scholes 63, David Beckham 66, Ole Gunnar Solskjær 73 | 61,611 |
| 4 Apr 2000 | Champions League | A | Real Madrid C.F. | 0–0 | |||
| 10 Apr 2000 | Premier League | A | Middlesbrough | Middlesbrough 1999–00 | 4–3 | Ryan Giggs 46, Andy Cole 60, Paul Scholes 74, Quinton Fortune 88 | 34,775 |
| 15 Apr 2000 | Premier League | H | Sunderland | Sunderland 1999–00 | 4–0 | Ole Gunnar Solskjær 3, Ole Gunnar Solskjær 51, Nicky Butt 65, Henning Berg 70 | 61,612 |
| 19 Apr 2000 | Champions League | H | Real Madrid C.F. | 2–3 | |||
| 22 Apr 2000 | Premier League | A | Southampton | Southampton 1999–00 | 3–1 | David Beckham 8, Francis Benali 15, Ole Gunnar Solskjær 30 | 15,245 |
| 24 Apr 2000 | Premier League | H | Chelsea | Chelsea 1999–00 | 3–2 | Dwight Yorke 11, Ole Gunnar Solskjær 40, Dwight Yorke 69 | 61,593 |
| 29 Apr 2000 | Premier League | A | Watford | Watford 1999–00 | 3–2 | Dwight Yorke 69, Ryan Giggs 71, Jordi Cruyff 87 | 20,250 |
| 6 May 2000 | Premier League | H | Tottenham Hotspur | Tottenham Hotspur 1999–00 | 3–1 | Ole Gunnar Solskjær 5, David Beckham 34, Teddy Sheringham 36 | 61,629 |
| 14 May 2000 | Premier League | A | Aston Villa | Aston Villa 1999–00 | 1–0 | Teddy Sheringham 65 | 39,217 |
97 of the goals in this season carry a named scorer.
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