Every competitive match Tottenham Hotspur played in 1989–90, in First Division — 46 matches, 22 won, 8 drawn, 16 lost, with scorers and attendances where the record holds them.
| Date | Competition | Venue | Opponent | Their season | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 19 Aug 1989 | First Division | H | Luton Town | Luton Town 1989–90 | 2–1 | Paul Stewart 29, Paul Allen 80 | 17,668 |
| 22 Aug 1989 | First Division | A | Everton | Everton 1989–90 | 1–2 | Paul Allen 19 | 34,402 |
| 26 Aug 1989 | First Division | A | Manchester City | Manchester City 1989–90 | 1–1 | Paul Gascoigne 37 | 32,004 |
| 9 Sep 1989 | First Division | A | Aston Villa | Aston Villa 1989–90 | 0–2 | 24,769 | |
| 16 Sep 1989 | First Division | H | Chelsea | Chelsea 1989–90 | 1–4 | Paul Gascoigne 61 | 16,260 |
| 20 Sep 1989 | League Cup | H | Southend United | 1–0 | Terry Fenwick | 15,734 | |
| 23 Sep 1989 | First Division | A | Norwich City | Norwich City 1989–90 | 2–2 | Paul Gascoigne 20, Gary Lineker 34 | 20,095 |
| 30 Sep 1989 | First Division | H | Queens Park Rangers | Queens Park Rangers 1989–90 | 3–2 | Gary Lineker 32, Gary Lineker 38, Gary Lineker 87 | 23,781 |
| 4 Oct 1989 | League Cup | A | Southend United | 2–3 | Paul Allen, Nayim | 10,400 | |
| 14 Oct 1989 | First Division | A | Charlton Athletic | Charlton Athletic 1989–90 | 3–1 | Mitchell Thomas 73, Gary Lineker 83, Paul Gascoigne 87 | 17,692 |
| 18 Oct 1989 | First Division | H | Arsenal | Arsenal 1989–90 | 2–1 | Vinny Samways 34, Paul Walsh 37 | 33,944 |
| 21 Oct 1989 | First Division | H | Sheffield Wednesday | Sheffield Wednesday 1989–90 | 3–0 | Gary Lineker 21, Gary Lineker 42, Paul Moran 64 | 26,909 |
| 25 Oct 1989 | League Cup | A | Manchester United | Manchester United 1989–90 | 3–0 | Vinny Samways, Gary Lineker, Nayim | 45,759 |
| 29 Oct 1989 | First Division | A | Liverpool | Liverpool 1989–90 | 0–1 | 36,550 | |
| 4 Nov 1989 | First Division | A | Southampton | Southampton 1989–90 | 1–1 | Paul Gascoigne 43 | 19,601 |
| 11 Nov 1989 | First Division | H | Wimbledon | Wimbledon 1989–90 | 0–1 | 26,876 | |
| 18 Nov 1989 | First Division | A | Crystal Palace | Crystal Palace 1989–90 | 3–2 | David Howells 23, Gary Lineker 25, Vinny Samways 76 | 26,266 |
| 22 Nov 1989 | League Cup | A | Tranmere Rovers | Tranmere Rovers 1989–90 | 2–2 | Paul Gascoigne, Dave Higgins | 13,789 |
| 25 Nov 1989 | First Division | H | Derby County | Derby County 1989–90 | 1–2 | Paul Stewart 4 | 28,075 |
| 29 Nov 1989 | League Cup | H | Tranmere Rovers | Tranmere Rovers 1989–90 | 4–0 | David Howells, Gary Mabbutt, Paul Stewart, Paul Allen | 23,724 |
| 2 Dec 1989 | First Division | A | Luton Town | Luton Town 1989–90 | 0–0 | 12,620 | |
| 9 Dec 1989 | First Division | H | Everton | Everton 1989–90 | 2–1 | Gary Lineker 24, Paul Stewart 60 | 29,374 |
| 16 Dec 1989 | First Division | A | Manchester United | Manchester United 1989–90 | 1–0 | Gary Lineker 69 | 36,230 |
| 26 Dec 1989 | First Division | H | Millwall | Millwall 1989–90 | 3–1 | Vinny Samways 8, Alan McLeary 18, Gary Lineker 35 | 26,874 |
| 30 Dec 1989 | First Division | H | Nottingham Forest | Nottingham Forest 1989–90 | 2–3 | Gary Lineker 11, Gary Lineker 89 | 33,401 |
| 1 Jan 1990 | First Division | A | Coventry City | Coventry City 1989–90 | 0–0 | 19,559 | |
| 6 Jan 1990 | FA Cup | H | Southampton | Southampton 1989–90 | 1–3 | David Howells | 33,134 |
| 13 Jan 1990 | First Division | H | Manchester City | Manchester City 1989–90 | 1–1 | David Howells 44 | 26,384 |
| 17 Jan 1990 | League Cup | A | Nottingham Forest | Nottingham Forest 1989–90 | 2–2 | Gary Lineker, Steve Sedgley | 30,044 |
| 20 Jan 1990 | First Division | A | Arsenal | Arsenal 1989–90 | 0–1 | 46,132 | |
| 24 Jan 1990 | League Cup | H | Nottingham Forest | Nottingham Forest 1989–90 | 2–3 | Nayim, Paul Walsh | 32,357 |
| 4 Feb 1990 | First Division | H | Norwich City | Norwich City 1989–90 | 4–0 | Gary Lineker 24, David Howells 44, Gary Lineker 47, Gary Lineker 63 | 19,599 |
| 10 Feb 1990 | First Division | A | Chelsea | Chelsea 1989–90 | 2–1 | David Howells 44, Gary Lineker 88 | 28,130 |
| 21 Feb 1990 | First Division | H | Aston Villa | Aston Villa 1989–90 | 0–2 | 32,472 | |
| 24 Feb 1990 | First Division | A | Derby County | Derby County 1989–90 | 1–2 | John Moncur 84 | 19,676 |
| 3 Mar 1990 | First Division | H | Crystal Palace | Crystal Palace 1989–90 | 0–1 | 26,181 | |
| 10 Mar 1990 | First Division | H | Charlton Athletic | Charlton Athletic 1989–90 | 3–0 | John Polston 21, Gary Lineker 56, David Howells 77 | 21,204 |
| 17 Mar 1990 | First Division | A | Queens Park Rangers | Queens Park Rangers 1989–90 | 1–3 | Paul Walsh 54 | 17,434 |
| 21 Mar 1990 | First Division | H | Liverpool | Liverpool 1989–90 | 1–0 | Paul Stewart 83 | 25,656 |
| 31 Mar 1990 | First Division | A | Sheffield Wednesday | Sheffield Wednesday 1989–90 | 4–2 | Paul Allen 3, Gary Lineker 60, Gary Lineker 62, Paul Stewart 70 | 26,582 |
| 7 Apr 1990 | First Division | A | Nottingham Forest | Nottingham Forest 1989–90 | 3–1 | Paul Stewart 9, Paul Allen 44, Paul Allen 71 | 21,668 |
| 14 Apr 1990 | First Division | H | Coventry City | Coventry City 1989–90 | 3–2 | Gary Lineker 33, Paul Stewart 45, Gary Lineker 69 | 23,917 |
| 16 Apr 1990 | First Division | A | Millwall | Millwall 1989–90 | 1–0 | Gary Lineker 50 | 10,574 |
| 21 Apr 1990 | First Division | H | Manchester United | Manchester United 1989–90 | 2–1 | Paul Gascoigne 21, Gary Lineker 25 | 33,317 |
| 28 Apr 1990 | First Division | A | Wimbledon | Wimbledon 1989–90 | 0–1 | 12,800 | |
| 5 May 1990 | First Division | H | Southampton | Southampton 1989–90 | 2–1 | Paul Stewart 21, Paul Allen 34 | 31,038 |
76 of the goals in this season carry a named scorer.
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