Every competitive match Tranmere Rovers played in 1999–00, in First Division — 60 matches, 25 won, 12 drawn, 23 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 | Bolton Wanderers | Bolton Wanderers 1999–00 | 0–0 | 7,674 | |
| 10 Aug 1999 | League Cup | A | Blackpool | Blackpool 1999–00 | 1–2 | Phil Thompson 21 | 3,298 |
| 14 Aug 1999 | First Division | A | Stockport County | Stockport County 1999–00 | 1–2 | Nick Henry 30 | 6,555 |
| 21 Aug 1999 | First Division | H | Huddersfield Town | Huddersfield Town 1999–00 | 1–0 | Jason Koumas 8 | 6,728 |
| 24 Aug 1999 | League Cup | H | Blackpool | Blackpool 1999–00 | 3–1 | ||
| 28 Aug 1999 | First Division | A | Port Vale | Port Vale 1999–00 | 0–1 | 4,657 | |
| 30 Aug 1999 | First Division | H | Sheffield United | Sheffield United 1999–00 | 1–3 | Steve Yates 35 | 5,436 |
| 3 Sep 1999 | First Division | A | Barnsley | Barnsley 1999–00 | 0–3 | 12,865 | |
| 11 Sep 1999 | First Division | A | Blackburn Rovers | Blackburn Rovers 1999–00 | 0–2 | 17,899 | |
| 14 Sep 1999 | League Cup | H | Coventry City | Coventry City 1999–00 | 5–1 | Scott Taylor 50, David Kelly 58, David Kelly 63, David Kelly 80, Scott Taylor 90 | 6,759 |
| 18 Sep 1999 | First Division | H | Portsmouth | Portsmouth 1999–00 | 2–4 | David Kelly 82, Dave Challinor 90 | 5,870 |
| 22 Sep 1999 | League Cup | A | Coventry City | Coventry City 1999–00 | 1–3 | Scott Taylor 22 | 12,433 |
| 25 Sep 1999 | First Division | H | Charlton Athletic | Charlton Athletic 1999–00 | 2–2 | Georges Santos 30, Wayne Allison 86 | 5,846 |
| 3 Oct 1999 | First Division | A | Crewe Alexandra | Crewe Alexandra 1999–00 | 2–0 | Wayne Allison 76, Wayne Allison 85 | 6,169 |
| 9 Oct 1999 | First Division | A | Queens Park Rangers | Queens Park Rangers 1999–00 | 1–2 | Clint Hill 54 | 9,357 |
| 12 Oct 1999 | League Cup | H | Oxford United | Oxford United 1999–00 | 2–0 | Steve Yates 57, Tony Grant 63 | 5,328 |
| 16 Oct 1999 | First Division | H | Manchester City | Manchester City 1999–00 | 1–1 | Alan Mahon 82 | 13,208 |
| 19 Oct 1999 | First Division | H | Grimsby Town | Grimsby Town 1999–00 | 3–2 | Wayne Allison 12, Wayne Allison 31, Gary Jones 59 | 5,004 |
| 23 Oct 1999 | First Division | A | Crystal Palace | Crystal Palace 1999–00 | 2–2 | Gary Jones 82, Andy Parkinson 90 | 18,645 |
| 26 Oct 1999 | First Division | A | Charlton Athletic | Charlton Athletic 1999–00 | 2–3 | Gareth Roberts 37, Andy Parkinson 38 | 19,491 |
| 30 Oct 1999 | First Division | H | Crewe Alexandra | Crewe Alexandra 1999–00 | 2–0 | Clint Hill 63, Wayne Allison 80 | 5,917 |
| 6 Nov 1999 | First Division | H | West Bromwich Albion | West Bromwich Albion 1999–00 | 3–0 | Andy Parkinson 34, Andy Parkinson 38, Alan Mahon 82 | 6,623 |
| 12 Nov 1999 | First Division | A | Ipswich Town | Ipswich Town 1999–00 | 0–0 | 14,514 | |
| 20 Nov 1999 | First Division | H | Nottingham Forest | Nottingham Forest 1999–00 | 3–0 | Clint Hill 53, Wayne Allison 66, David Kelly 90 | 6,693 |
| 23 Nov 1999 | First Division | A | Birmingham City | Birmingham City 1999–00 | 1–3 | Martin Grainger 78 | 21,132 |
| 27 Nov 1999 | First Division | H | Wolverhampton Wanderers | Wolverhampton Wanderers 1999–00 | 1–0 | Wayne Allison 50 | 8,017 |
| 30 Nov 1999 | League Cup | H | Barnsley | Barnsley 1999–00 | 4–0 | Andy Parkinson 3, Alan Morgan 45, Clint Hill 56, Michael Black 86 | 7,039 |
| 4 Dec 1999 | First Division | A | Bolton Wanderers | Bolton Wanderers 1999–00 | 3–2 | Andy Parkinson 18, Dave Challinor 63, Scott Taylor 79 | 13,534 |
| 11 Dec 1999 | FA Cup | H | West Ham United | West Ham United 1999–00 | 1–0 | Nick Henry 21 | 13,629 |
| 14 Dec 1999 | League Cup | H | Middlesbrough | Middlesbrough 1999–00 | 2–1 | David Kelly 39, Andy Parkinson 71 | 10,581 |
| 17 Dec 1999 | First Division | H | Norwich City | Norwich City 1999–00 | 1–2 | Wayne Allison 14 | 5,863 |
| 26 Dec 1999 | First Division | A | Walsall | Walsall 1999–00 | 2–1 | Andy Parkinson 67, Wayne Allison 74 | 7,214 |
| 28 Dec 1999 | First Division | H | Swindon Town | Swindon Town 1999–00 | 3–1 | Clint Hill 11, Wayne Allison 13, Wayne Allison 26 | 8,068 |
| 3 Jan 2000 | First Division | A | Fulham | Fulham 1999–00 | 0–1 | 11,377 | |
| 8 Jan 2000 | FA Cup | H | Sunderland | Sunderland 1999–00 | 1–0 | Wayne Allison 25 | 15,468 |
| 12 Jan 2000 | League Cup | A | Bolton Wanderers | Bolton Wanderers 1999–00 | 1–0 | Clint Hill 22 | 13,303 |
| 15 Jan 2000 | First Division | H | Stockport County | Stockport County 1999–00 | 0–0 | 7,565 | |
| 22 Jan 2000 | First Division | A | Huddersfield Town | Huddersfield Town 1999–00 | 0–1 | 12,653 | |
| 26 Jan 2000 | League Cup | H | Bolton Wanderers | Bolton Wanderers 1999–00 | 3–0 | Nick Henry 5, Alan Mahon 20, David Kelly 70 | 15,864 |
| 29 Jan 2000 | FA Cup | A | Fulham | Fulham 1999–00 | 2–1 | Wayne Allison 9, David Kelly 70 | 13,859 |
| 5 Feb 2000 | First Division | A | Sheffield United | Sheffield United 1999–00 | 1–3 | Scott Taylor 57 | 14,219 |
| 11 Feb 2000 | First Division | H | Barnsley | Barnsley 1999–00 | 2–2 | Andy Parkinson 16, David Kelly 57 | 7,127 |
| 16 Feb 2000 | First Division | A | Wolverhampton Wanderers | Wolverhampton Wanderers 1999–00 | 0–4 | 18,186 | |
| 20 Feb 2000 | FA Cup | H | Newcastle United | Newcastle United 1999–00 | 2–3 | Wayne Allison 45, Gary Jones 76 | 15,776 |
| 27 Feb 2000 | League Cup | N | Leicester City | Leicester City 1999–00 | 1–2 | David Kelly 77 | 74,313 |
| 1 Mar 2000 | First Division | A | Portsmouth | Portsmouth 1999–00 | 2–1 | Reuben Hazell 33, Steve Yates 90 | 10,759 |
| 4 Mar 2000 | First Division | H | Blackburn Rovers | Blackburn Rovers 1999–00 | 2–1 | Alan Mahon 47, Wayne Allison 90 | 9,502 |
| 7 Mar 2000 | First Division | A | West Bromwich Albion | West Bromwich Albion 1999–00 | 0–2 | 11,958 | |
| 11 Mar 2000 | First Division | H | Birmingham City | Birmingham City 1999–00 | 2–1 | Jason Koumas 4, Gary Jones 83 | 9,232 |
| 18 Mar 2000 | First Division | A | Nottingham Forest | Nottingham Forest 1999–00 | 1–1 | Wayne Allison 34 | 4,428 |
| 22 Mar 2000 | First Division | H | Ipswich Town | Ipswich Town 1999–00 | 0–2 | 6,933 | |
| 25 Mar 2000 | First Division | H | Walsall | Walsall 1999–00 | 1–1 | Wayne Allison 4 | 6,537 |
| 1 Apr 2000 | First Division | A | Norwich City | Norwich City 1999–00 | 1–1 | Daryl Sutch 38 | 13,734 |
| 9 Apr 2000 | First Division | H | Fulham | Fulham 1999–00 | 1–1 | David Kelly 72 | 7,132 |
| 15 Apr 2000 | First Division | A | Swindon Town | Swindon Town 1999–00 | 1–3 | Clint Hill 37 | 4,925 |
| 18 Apr 2000 | First Division | H | Port Vale | Port Vale 1999–00 | 2–1 | David Kelly 60, David Kelly 89 | 5,602 |
| 22 Apr 2000 | First Division | A | Manchester City | Manchester City 1999–00 | 0–2 | 32,842 | |
| 24 Apr 2000 | First Division | H | Queens Park Rangers | Queens Park Rangers 1999–00 | 1–1 | Alan Mahon 52 | 7,744 |
| 29 Apr 2000 | First Division | A | Grimsby Town | Grimsby Town 1999–00 | 2–1 | Dave Challinor 12, Wayne Allison 82 | 5,427 |
| 7 May 2000 | First Division | H | Crystal Palace | Crystal Palace 1999–00 | 1–2 | Scott Taylor 46 | 8,891 |
83 of the goals in this season carry a named scorer.
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