| Club: | Grimsby Town |
| Season: | 1999–2000 |
| Manager: | Alan Buckley |
| Chairman: | Bill Carr |
| Stadium: | Blundell Park |
| League: | First Division |
| League Result: | 20th |
| Cup1: | FA Cup |
| Cup1 Result: | Fourth round |
| Cup2: | League Cup |
| Cup2 Result: | Third round |
| League Topscorer: | Ashcroft (12) |
| Season Topscorer: | Ashcroft (13) |
| Average Attendance: | 6,157 |
| Prevseason: | 1998–99 |
| Nextseason: | 2000–01 |
During the 1999–2000 English football season, Grimsby Town F.C. competed in the Football League First Division.
After a brilliant first full season back in the second tier finishing 11th, Grimsby a season later really struggled and finished the 1999–2000 season in 20th, avoiding relegation at the expense of Buckley's former club Walsall.
| Date | Pos | Player | Transferred from | Fee | Ref | |
|---|---|---|---|---|---|---|
| 9 July 1999 | FW | Bradley Allen | Charlton Athletic | Free Transfer | ||
| 10 July 1999 | GK | Danny Coyne | Tranmere Rovers | Free Transfer | ||
| 9 September 1999 | MF | Alan Pouton | York City | £150,000 | ||
| 1 August 1999 | MF | Matt McKenzie | Dunkirk | Free Transfer |
| Date | Pos | Player | Transferred from | Date Until | Ref | |
|---|---|---|---|---|---|---|
| 5 August 1999 | MF | Alan Pouton | York City | 8 September 1999 | ||
| 4 November 1999 | MF | Ian Hamilton | Sheffield United | 4 December 1999 | ||
| 24 February 2000 | FW | Mark Nicholls | Chelsea | 28 March 2000 |
| Date | Pos | Player | Transferred To | Fee | Ref | |
|---|---|---|---|---|---|---|
| 18 June 1999 | MF | Tommy Widdrington | Port Vale | Free Transfer | ||
| 1 July 1999 | MF | Jim Dobbin | Gainsborough Trinity | Released | ||
| 13 July 1999 | FW | Lee Nogan | Darlington | Released | ||
| 6 August 1999 | GK | Aidan Davison | Sheffield United | Free Transfer | ||
| 28 January 2000 | FW | Jack Lester | Nottingham Forest | £300,000 |
| Date | Pos | Player | Transferred To | Date Until | Ref |
|---|---|---|---|---|---|
| 1 August 1999 | GK | Andy Love | Ilkeston Town | 1 October 1999 | |
| 10 November 1999 | FW |  Daryl Clare | Northampton Town | 29 January 2000 | |
| 19 February 2000 | GK | Andy Love | Ilkeston Town | 8 May 2000 |
See main article: 1999–2000 Football League.
Grimsby Town's score comes first[1]
| Win | Draw | Loss |
| Date | Opponent | Venue | Result | Attendance | Scorers | |
|---|---|---|---|---|---|---|
| 7 August 1999 | Stockport County | H | 0–1 | 5,528 | ||
| 14 August 1999 | Nottingham Forest | A | 1–2 | 17,121 | Groves (pen) | |
| 21 August 1999 | Fulham | H | 1–1 | 6,196 | Black | |
| 27 August 1999 | Crewe Alexandra | A | 1–1 | 5,440 | Lester | |
| 30 August 1999 | Swindon Town | H | 1–0 | 5,705 | Groves (pen) | |
| 5 September 1999 | Port Vale | A | 1–3 | 3,737 | Allen | |
| 11 September 1999 | Walsall | H | 1–0 | 6,014 | Allen | |
| 18 September 1999 | Crystal Palace | A | 0–3 | 13,294 | ||
| 25 September 1999 | Portsmouth | A | 2–1 | 12,073 | Ashcroft, Coldicott | |
| 2 October 1999 | Ipswich Town | H | 2–1 | 6,531 | Donovan, Ashcroft | |
| 16 October 1999 | Blackburn Rovers | A | 1–1 | 17,575 | Ashcroft (pen) | |
| 19 October 1999 | Tranmere Rovers | A | 2–3 | 5,004 | Allen (2) | |
| 23 October 1999 | Birmingham City | H | 1–1 | 6,266 | Allen | |
| 26 October 1999 | Portsmouth | H | 1–0 | 5,912 | Awford (own goal) | |
| 30 October 1999 | Ipswich Town | A | 0–2 | 16,617 | ||
| 6 November 1999 | Wolverhampton Wanderers | A | 0–3 | 19,036 | ||
| 12 November 1999 | Charlton Athletic | H | 2–5 | 6,849 | Ashcroft (pen), Donovan | |
| 20 November 1999 | Bolton Wanderers | A | 0–2 | 12,415 | ||
| 23 November 1999 | Queens Park Rangers | H | 2–1 | 4,297 | Ashcroft (2 pens) | |
| 28 November 1999 | Norwich City | H | 2–1 | 5,333 | Ashcroft (2, 1 pen) | |
| 4 December 1999 | Stockport County | A | 1–2 | 5,581 | Hamilton | |
| 14 December 1999 | West Bromwich Albion | H | 1–1 | 4,036 | Allen | |
| 18 December 1999 | Huddersfield Town | A | 1–3 | 14,065 | Groves | |
| 26 December 1999 | Barnsley | H | 0–3 | 8,742 | ||
| 28 December 1999 | Manchester City | A | 1–2 | 32,607 | Coldicott | |
| 3 January 2000 | Sheffield United | H | 2–2 | 7,618 | Lester, Ashcroft | |
| 15 January 2000 | Nottingham Forest | H | 4–3 | 6,738 | Lester, Ashcroft (2, 1 pen), Donovan | |
| 22 January 2000 | Fulham | A | 1–0 | 10,802 | Lester | |
| 29 January 2000 | Crewe Alexandra | H | 1–1 | 6,147 | Allen | |
| 5 February 2000 | Swindon Town | A | 1–0 | 5,784 | Ashcroft | |
| 12 February 2000 | Port Vale | H | 2–0 | 6,265 | Clare, Allen | |
| 19 February 2000 | Norwich City | A | 0–3 | 13,533 | ||
| 26 February 2000 | Crystal Palace | H | 1–0 | 5,421 | D Smith (pen) | |
| 4 March 2000 | Walsall | A | 0–1 | 5,384 | ||
| 7 March 2000 | Wolverhampton Wanderers | H | 1–0 | 5,575 | Clare | |
| 11 March 2000 | Queens Park Rangers | A | 0–1 | 10,450 | ||
| 18 March 2000 | Bolton Wanderers | H | 0–1 | 5,289 | ||
| 22 March 2000 | Charlton Athletic | A | 0–4 | 19,364 | ||
| 27 March 2000 | Barnsley | A | 0–3 | 14,613 | ||
| 1 April 2000 | Huddersfield Town | H | 0–0 | 6,993 | ||
| 8 April 2000 | Sheffield United | A | 0–0 | 11,612 | ||
| 15 April 2000 | Manchester City | H | 1–1 | 8,166 | Pouton | |
| 22 April 2000 | Blackburn Rovers | H | 0–0 | 6,558 | ||
| 24 April 2000 | West Bromwich Albion | A | 1–2 | 15,291 | Black | |
| 29 April 2000 | Tranmere Rovers | H | 1–2 | 5,427 | Clare | |
| 7 May 2000 | Birmingham City | A | 0–0 | 25,263 |
See main article: 1999–2000 FA Cup.
| 10 December 1999 | Stockport County | H | 3–2 | 3,400 | Livingstone (2), Allen | ||
| 8 January 2000 | Bolton Wanderers | H | 0–2 | 4,270 |
See main article: 1999–2000 Football League Cup.
| 10 August 1999 | Carlisle United | A | 0–0 | 3,000 | |||
| 24 August 1999 | Carlisle United | H | 6–0 (won 6–0 on agg) | 2,696 | Lester (3), Groves, Coldicott, Donovan | ||
| 14 September 1999 | Leyton Orient | H | 4–1 | 2,238 | D Smith, Gallimore, Ashcroft (pen), Groves | ||
| 21 September 1999 | Leyton Orient | A | 0–1 (won 4–2 on agg) | 1,036 | |||
| 13 October 1999 | Leicester City | A | 0–2 | 13,701 |