Every competitive match Tottenham Hotspur played in 1999–00, in Premier League — 46 matches, 18 won, 10 drawn, 18 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 | West Ham United | West Ham United 1999–00 | 0–1 | 26,010 | |
| 9 Aug 1999 | Premier League | H | Newcastle United | Newcastle United 1999–00 | 3–1 | Steffen Iversen, Les Ferdinand, Tim Sherwood | 28,701 |
| 14 Aug 1999 | Premier League | H | Everton | Everton 1999–00 | 3–2 | Tim Sherwood, Øyvind Leonhardsen, Steffen Iversen | 34,539 |
| 21 Aug 1999 | Premier League | A | Sheffield Wednesday | Sheffield Wednesday 1999–00 | 2–1 | Les Ferdinand, Øyvind Leonhardsen | 24,027 |
| 28 Aug 1999 | Premier League | H | Leeds United | Leeds United 1999–00 | 1–2 | Tim Sherwood | 36,012 |
| 12 Sep 1999 | Premier League | A | Bradford City | Bradford City 1999–00 | 1–1 | Chris Perry | 18,143 |
| 16 Sep 1999 | UEFA Cup | H | Zimbru Chişinău | 3–0 | Øyvind Leonhardsen, Chris Perry, Tim Sherwood | 32,660 | |
| 19 Sep 1999 | Premier League | H | Coventry City | Coventry City 1999–00 | 3–2 | Steffen Iversen, Chris Armstrong, Øyvind Leonhardsen | 35,224 |
| 26 Sep 1999 | Premier League | A | Wimbledon | Wimbledon 1999–00 | 1–1 | Stephen Carr | 17,368 |
| 30 Sep 1999 | UEFA Cup | A | Zimbru Chişinău | 0–0 | 7,000 | ||
| 3 Oct 1999 | Premier League | H | Leicester City | Leicester City 1999–00 | 2–3 | Steffen Iversen, Steffen Iversen | 35,591 |
| 13 Oct 1999 | League Cup | H | Crewe Alexandra | Crewe Alexandra 1999–00 | 3–1 | Øyvind Leonhardsen, David Ginola, Tim Sherwood | 25,486 |
| 16 Oct 1999 | Premier League | A | Derby County | Derby County 1999–00 | 1–0 | Chris Armstrong | 29,815 |
| 23 Oct 1999 | Premier League | H | Manchester United | Manchester United 1999–00 | 3–1 | Steffen Iversen, Paul Scholes, Stephen Carr | 36,072 |
| 28 Oct 1999 | UEFA Cup | H | 1. FC Kaiserslautern | 1–0 | Steffen Iversen | 35,486 | |
| 31 Oct 1999 | Premier League | A | Sunderland | Sunderland 1999–00 | 1–2 | Steffen Iversen | 41,904 |
| 4 Nov 1999 | UEFA Cup | A | 1. FC Kaiserslautern | 0–2 | 32,000 | ||
| 7 Nov 1999 | Premier League | H | Arsenal | Arsenal 1999–00 | 2–1 | Steffen Iversen, Tim Sherwood | 36,085 |
| 20 Nov 1999 | Premier League | A | Southampton | Southampton 1999–00 | 1–0 | Øyvind Leonhardsen | 15,248 |
| 28 Nov 1999 | Premier League | A | Newcastle United | Newcastle United 1999–00 | 1–2 | Chris Armstrong | 36,460 |
| 1 Dec 1999 | League Cup | A | Fulham | Fulham 1999–00 | 1–3 | Steffen Iversen | 18,134 |
| 6 Dec 1999 | Premier League | H | West Ham United | West Ham United 1999–00 | 0–0 | 36,233 | |
| 12 Dec 1999 | FA Cup | H | Newcastle United | Newcastle United 1999–00 | 1–1 | Steffen Iversen | 33,116 |
| 18 Dec 1999 | Premier League | A | Middlesbrough | Middlesbrough 1999–00 | 1–2 | Ramon Vega | 33,129 |
| 22 Dec 1999 | FA Cup | A | Newcastle United | Newcastle United 1999–00 | 1–6 | David Ginola | 35,415 |
| 26 Dec 1999 | Premier League | H | Watford | Watford 1999–00 | 4–0 | David Ginola, Steffen Iversen, Tim Sherwood, Tim Sherwood | 36,089 |
| 29 Dec 1999 | Premier League | A | Aston Villa | Aston Villa 1999–00 | 1–1 | Tim Sherwood | 39,217 |
| 3 Jan 2000 | Premier League | H | Liverpool | Liverpool 1999–00 | 1–0 | Chris Armstrong | 36,044 |
| 12 Jan 2000 | Premier League | A | Chelsea | Chelsea 1999–00 | 0–1 | 34,969 | |
| 15 Jan 2000 | Premier League | A | Everton | Everton 1999–00 | 2–2 | Chris Armstrong, David Ginola | 36,144 |
| 22 Jan 2000 | Premier League | H | Sheffield Wednesday | Sheffield Wednesday 1999–00 | 0–1 | 35,897 | |
| 5 Feb 2000 | Premier League | H | Chelsea | Chelsea 1999–00 | 0–1 | 36,041 | |
| 12 Feb 2000 | Premier League | A | Leeds United | Leeds United 1999–00 | 0–1 | 40,127 | |
| 26 Feb 2000 | Premier League | A | Coventry City | Coventry City 1999–00 | 1–0 | Chris Armstrong | 23,077 |
| 4 Mar 2000 | Premier League | H | Bradford City | Bradford City 1999–00 | 1–1 | Steffen Iversen | 35,472 |
| 11 Mar 2000 | Premier League | H | Southampton | Southampton 1999–00 | 7–2 | Dean Richards, Darren Anderton, Chris Armstrong, Chris Armstrong, Steffen Iversen, Steffen Iversen, Steffen Iversen | 36,024 |
| 19 Mar 2000 | Premier League | A | Arsenal | Arsenal 1999–00 | 1–2 | Chris Armstrong | 38,131 |
| 25 Mar 2000 | Premier League | A | Watford | Watford 1999–00 | 1–1 | Chris Armstrong | 20,050 |
| 3 Apr 2000 | Premier League | H | Middlesbrough | Middlesbrough 1999–00 | 2–3 | Chris Armstrong, David Ginola | 31,796 |
| 9 Apr 2000 | Premier League | A | Liverpool | Liverpool 1999–00 | 0–2 | 44,536 | |
| 15 Apr 2000 | Premier League | H | Aston Villa | Aston Villa 1999–00 | 2–4 | Steffen Iversen, Chris Armstrong | 35,304 |
| 19 Apr 2000 | Premier League | A | Leicester City | Leicester City 1999–00 | 1–0 | David Ginola | 19,764 |
| 22 Apr 2000 | Premier League | H | Wimbledon | Wimbledon 1999–00 | 2–0 | Chris Armstrong, Darren Anderton | 33,086 |
| 29 Apr 2000 | Premier League | H | Derby County | Derby County 1999–00 | 1–1 | Stephen Clemence | 33,044 |
| 6 May 2000 | Premier League | A | Manchester United | Manchester United 1999–00 | 1–3 | Chris Armstrong | 61,629 |
| 14 May 2000 | Premier League | H | Sunderland | Sunderland 1999–00 | 3–1 | Darren Anderton, Tim Sherwood, Stephen Carr | 36,070 |
67 of the goals in this season carry a named scorer.
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