Every competitive match Grimsby Town played in 1999–00, in First Division — 53 matches, 16 won, 13 drawn, 24 lost, with scorers and attendances where the record holds them.
| Date | Competition | Venue | Opponent | Their season | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 7 Aug 1999 | First Division | H | Stockport County | Stockport County 1999–00 | 0–1 | 5,528 | |
| 10 Aug 1999 | League Cup | A | Carlisle United | Carlisle United 1999–00 | 0–0 | 3,000 | |
| 14 Aug 1999 | First Division | A | Nottingham Forest | Nottingham Forest 1999–00 | 1–2 | Paul Groves | 17,121 |
| 21 Aug 1999 | First Division | H | Fulham | Fulham 1999–00 | 1–1 | Kingsley Black | 6,196 |
| 24 Aug 1999 | League Cup | H | Carlisle United | Carlisle United 1999–00 | 6–0 | Jack Lester, Jack Lester, Jack Lester, Paul Groves, Stacy Coldicott, Kevin Donovan | 2,696 |
| 27 Aug 1999 | First Division | A | Crewe Alexandra | Crewe Alexandra 1999–00 | 1–1 | Jack Lester | 5,440 |
| 30 Aug 1999 | First Division | H | Swindon Town | Swindon Town 1999–00 | 1–0 | Paul Groves | 5,705 |
| 5 Sep 1999 | First Division | A | Port Vale | Port Vale 1999–00 | 1–3 | Bradley Allen | 3,737 |
| 11 Sep 1999 | First Division | H | Walsall | Walsall 1999–00 | 1–0 | Bradley Allen | 6,014 |
| 14 Sep 1999 | League Cup | H | Leyton Orient | Leyton Orient 1999–00 | 4–1 | David Smith, Tony Gallimore, Lee Ashcroft, Paul Groves | 2,238 |
| 18 Sep 1999 | First Division | A | Crystal Palace | Crystal Palace 1999–00 | 0–3 | 13,294 | |
| 21 Sep 1999 | League Cup | A | Leyton Orient | Leyton Orient 1999–00 | 0–1 | 1,036 | |
| 25 Sep 1999 | First Division | A | Portsmouth | Portsmouth 1999–00 | 2–1 | Lee Ashcroft, Stacy Coldicott | 12,073 |
| 2 Oct 1999 | First Division | H | Ipswich Town | Ipswich Town 1999–00 | 2–1 | Kevin Donovan, Lee Ashcroft | 6,531 |
| 13 Oct 1999 | League Cup | A | Leicester City | Leicester City 1999–00 | 0–2 | 13,701 | |
| 16 Oct 1999 | First Division | A | Blackburn Rovers | Blackburn Rovers 1999–00 | 1–1 | Lee Ashcroft | 17,575 |
| 19 Oct 1999 | First Division | A | Tranmere Rovers | Tranmere Rovers 1999–00 | 2–3 | Bradley Allen, Bradley Allen | 5,004 |
| 23 Oct 1999 | First Division | H | Birmingham City | Birmingham City 1999–00 | 1–1 | Bradley Allen | 6,266 |
| 26 Oct 1999 | First Division | H | Portsmouth | Portsmouth 1999–00 | 1–0 | Andy Awford | 5,912 |
| 30 Oct 1999 | First Division | A | Ipswich Town | Ipswich Town 1999–00 | 0–2 | 16,617 | |
| 6 Nov 1999 | First Division | A | Wolverhampton Wanderers | Wolverhampton Wanderers 1999–00 | 0–3 | 19,036 | |
| 12 Nov 1999 | First Division | H | Charlton Athletic | Charlton Athletic 1999–00 | 2–5 | Lee Ashcroft, Kevin Donovan | 6,849 |
| 20 Nov 1999 | First Division | A | Bolton Wanderers | Bolton Wanderers 1999–00 | 0–2 | 12,415 | |
| 23 Nov 1999 | First Division | H | Queens Park Rangers | Queens Park Rangers 1999–00 | 2–1 | Lee Ashcroft, Lee Ashcroft | 4,297 |
| 28 Nov 1999 | First Division | H | Norwich City | Norwich City 1999–00 | 2–1 | Lee Ashcroft, Lee Ashcroft | 5,333 |
| 4 Dec 1999 | First Division | A | Stockport County | Stockport County 1999–00 | 1–2 | Ian Hamilton | 5,581 |
| 11 Dec 1999 | FA Cup | H | Stockport County | Stockport County 1999–00 | 3–2 | Steve Livingstone, Steve Livingstone, Bradley Allen | 3,400 |
| 14 Dec 1999 | First Division | H | West Bromwich Albion | West Bromwich Albion 1999–00 | 1–1 | Bradley Allen | 4,036 |
| 18 Dec 1999 | First Division | A | Huddersfield Town | Huddersfield Town 1999–00 | 1–3 | Paul Groves | 14,065 |
| 26 Dec 1999 | First Division | H | Barnsley | Barnsley 1999–00 | 0–3 | 8,742 | |
| 28 Dec 1999 | First Division | A | Manchester City | Manchester City 1999–00 | 1–2 | Stacy Coldicott | 32,607 |
| 3 Jan 2000 | First Division | H | Sheffield United | Sheffield United 1999–00 | 2–2 | Jack Lester, Lee Ashcroft | 7,618 |
| 8 Jan 2000 | FA Cup | H | Bolton Wanderers | Bolton Wanderers 1999–00 | 0–2 | 4,270 | |
| 15 Jan 2000 | First Division | H | Nottingham Forest | Nottingham Forest 1999–00 | 4–3 | Jack Lester, Lee Ashcroft, Lee Ashcroft, Kevin Donovan | 6,738 |
| 22 Jan 2000 | First Division | A | Fulham | Fulham 1999–00 | 1–0 | Jack Lester | 10,802 |
| 29 Jan 2000 | First Division | H | Crewe Alexandra | Crewe Alexandra 1999–00 | 1–1 | Bradley Allen | 6,147 |
| 5 Feb 2000 | First Division | A | Swindon Town | Swindon Town 1999–00 | 1–0 | Lee Ashcroft | 5,784 |
| 12 Feb 2000 | First Division | H | Port Vale | Port Vale 1999–00 | 2–0 | Daryl Clare, Bradley Allen | 6,265 |
| 19 Feb 2000 | First Division | A | Norwich City | Norwich City 1999–00 | 0–3 | 13,533 | |
| 26 Feb 2000 | First Division | H | Crystal Palace | Crystal Palace 1999–00 | 1–0 | David Smith | 5,421 |
| 4 Mar 2000 | First Division | A | Walsall | Walsall 1999–00 | 0–1 | 5,384 | |
| 7 Mar 2000 | First Division | H | Wolverhampton Wanderers | Wolverhampton Wanderers 1999–00 | 1–0 | Daryl Clare | 5,575 |
| 11 Mar 2000 | First Division | A | Queens Park Rangers | Queens Park Rangers 1999–00 | 0–1 | 10,450 | |
| 18 Mar 2000 | First Division | H | Bolton Wanderers | Bolton Wanderers 1999–00 | 0–1 | 5,289 | |
| 22 Mar 2000 | First Division | A | Charlton Athletic | Charlton Athletic 1999–00 | 0–4 | 19,364 | |
| 27 Mar 2000 | First Division | A | Barnsley | Barnsley 1999–00 | 0–3 | 14,613 | |
| 1 Apr 2000 | First Division | H | Huddersfield Town | Huddersfield Town 1999–00 | 0–0 | 6,993 | |
| 8 Apr 2000 | First Division | A | Sheffield United | Sheffield United 1999–00 | 0–0 | 11,612 | |
| 15 Apr 2000 | First Division | H | Manchester City | Manchester City 1999–00 | 1–1 | Alan Pouton | 8,166 |
| 22 Apr 2000 | First Division | H | Blackburn Rovers | Blackburn Rovers 1999–00 | 0–0 | 6,558 | |
| 24 Apr 2000 | First Division | A | West Bromwich Albion | West Bromwich Albion 1999–00 | 1–2 | Kingsley Black | 15,291 |
| 29 Apr 2000 | First Division | H | Tranmere Rovers | Tranmere Rovers 1999–00 | 1–2 | Daryl Clare | 5,427 |
| 7 May 2000 | First Division | A | Birmingham City | Birmingham City 1999–00 | 0–0 | 25,263 |
54 of the goals in this season carry a named scorer.
All 130 Grimsby Town seasons · Grimsby Town head-to-head records · Grimsby Town players