Every competitive match Rotherham United played in 1999–00, in Third Division — 53 matches, 27 won, 12 drawn, 14 lost, with scorers and attendances where the record holds them.
| Date | Competition | Venue | Opponent | Their season | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 7 Aug 1999 | Third Division | A | Lincoln City | Lincoln City 1999–00 | 1–2 | Paul Warne 90 | 4,494 |
| 10 Aug 1999 | League Cup | H | Hull City | Hull City 1999–00 | 0–1 | 3,294 | |
| 14 Aug 1999 | Third Division | H | Chester | 4–0 | Gary Martindale 54, Gary Martindale 58, Leo Fortune-West 81, Kevin Watson 88 | 2,966 | |
| 21 Aug 1999 | Third Division | A | Exeter City | Exeter City 1999–00 | 1–3 | Darren Garner 23 | 2,646 |
| 24 Aug 1999 | League Cup | A | Hull City | Hull City 1999–00 | 0–2 | 4,373 | |
| 28 Aug 1999 | Third Division | H | Shrewsbury Town | Shrewsbury Town 1999–00 | 4–0 | Andy Turner 2, Rob Scott 3, Darren Garner 21, Darren Garner 33 | 2,708 |
| 30 Aug 1999 | Third Division | A | Macclesfield Town | 1–1 | Leo Fortune-West 86 | 2,307 | |
| 4 Sep 1999 | Third Division | H | York City | 1–0 | Darren Garner 59 | 3,171 | |
| 11 Sep 1999 | Third Division | A | Plymouth Argyle | Plymouth Argyle 1999–00 | 1–1 | Trevor Berry 49 | 4,075 |
| 18 Sep 1999 | Third Division | H | Rochdale | Rochdale 1999–00 | 0–1 | 3,568 | |
| 25 Sep 1999 | Third Division | H | Northampton Town | Northampton Town 1999–00 | 3–0 | Steve Thompson 14, Leo Fortune-West 52, Steve Thompson 80 | 3,625 |
| 2 Oct 1999 | Third Division | A | Cheltenham Town | Cheltenham Town 1999–00 | 2–0 | Steve Thompson 37, Paul Warne 47 | 3,331 |
| 12 Oct 1999 | Third Division | A | Swansea City | Swansea City 1999–00 | 0–2 | 5,287 | |
| 16 Oct 1999 | Third Division | H | Barnet | 2–0 | Leo Fortune-West 10, Chris Sedgwick 67 | 3,596 | |
| 19 Oct 1999 | Third Division | H | Hartlepool United | 3–0 | Darren Garner 7, Darren Garner 14, Trevor Berry 30 | 3,340 | |
| 23 Oct 1999 | Third Division | A | Northampton Town | Northampton Town 1999–00 | 1–0 | 5,753 | |
| 30 Oct 1999 | FA Cup | H | Worthing | 3–0 | |||
| 30 Oct 1999 | FA Cup | H | Woking | 3–0 | Steve Thompson 31, Darren Garner 81, Gary Martindale 90 | 3,716 | |
| 2 Nov 1999 | Third Division | H | Torquay United | 1–0 | Trevor Berry 27 | 3,892 | |
| 6 Nov 1999 | Third Division | A | Hull City | Hull City 1999–00 | 0–0 | 7,045 | |
| 12 Nov 1999 | Third Division | H | Leyton Orient | Leyton Orient 1999–00 | 0–1 | 4,280 | |
| 20 Nov 1999 | FA Cup | A | Burnley | Burnley 1999–00 | 0–2 | 8,110 | |
| 23 Nov 1999 | Third Division | A | Mansfield Town | Mansfield Town 1999–00 | 2–1 | Trevor Berry 27, Chris Sedgwick 90 | 2,937 |
| 27 Nov 1999 | Third Division | A | Carlisle United | Carlisle United 1999–00 | 1–0 | Paul Hurst 90 | 2,649 |
| 4 Dec 1999 | Third Division | H | Lincoln City | Lincoln City 1999–00 | 1–1 | Darren Garner 45 | 3,674 |
| 7 Dec 1999 | EFL Trophy | H | Shrewsbury Town | Shrewsbury Town 1999–00 | 2–1 | Gary Hanmer 18, Chris Sedgwick 72 | 1,166 |
| 11 Dec 1999 | Third Division | A | Halifax Town | 0–0 | 2,583 | ||
| 18 Dec 1999 | Third Division | H | Darlington | 2–1 | Jason White 83, Jason White 88 | 4,234 | |
| 26 Dec 1999 | Third Division | A | Peterborough United | Peterborough United 1999–00 | 5–0 | Danny Hudson 2, Paul Warne 34, Paul Warne 49, Steve Thompson 71, Leo Fortune-West 74 | 10,789 |
| 28 Dec 1999 | Third Division | H | Brighton & Hove Albion | Brighton & Hove Albion 1999–00 | 1–3 | Guy Branston 83 | 5,924 |
| 3 Jan 2000 | Third Division | A | Southend United | 2–1 | Leo Fortune-West 26, Leo Fortune-West 40 | 4,728 | |
| 8 Jan 2000 | Third Division | H | Halifax Town | 0–1 | 4,450 | ||
| 11 Jan 2000 | EFL Trophy | H | Chesterfield | Chesterfield 1999–00 | 1–4 | Jason White 61 | 1,997 |
| 15 Jan 2000 | Third Division | A | Chester | 2–0 | Paul Warne 21, Leo Fortune-West 54 | 3,398 | |
| 22 Jan 2000 | Third Division | H | Exeter City | Exeter City 1999–00 | 5–0 | Leo Fortune-West 5, Leo Fortune-West 7, Paul Warne 12, Brian Wilsterman 82, Paul Warne 86 | 3,402 |
| 29 Jan 2000 | Third Division | A | Shrewsbury Town | Shrewsbury Town 1999–00 | 0–0 | 2,587 | |
| 5 Feb 2000 | Third Division | H | Macclesfield Town | 2–1 | Chris Sedgwick 31, Leo Fortune-West 44 | 4,175 | |
| 12 Feb 2000 | Third Division | A | York City | 2–1 | Leo Fortune-West 7, Guy Branston 90 | 4,531 | |
| 19 Feb 2000 | Third Division | H | Carlisle United | Carlisle United 1999–00 | 4–2 | Leo Fortune-West 22, Leo Fortune-West 32, Brian Wilsterman 50, Leo Fortune-West 73 | 4,271 |
| 26 Feb 2000 | Third Division | A | Rochdale | Rochdale 1999–00 | 1–0 | Jason White 58 | 4,131 |
| 4 Mar 2000 | Third Division | H | Plymouth Argyle | Plymouth Argyle 1999–00 | 1–1 | Paul Warne 76 | 4,496 |
| 7 Mar 2000 | Third Division | H | Hull City | Hull City 1999–00 | 3–0 | Brian Wilsterman 74, Leo Fortune-West 76, Paul Warne 84 | 4,881 |
| 11 Mar 2000 | Third Division | A | Torquay United | 1–2 | Steve Thompson 42 | 2,655 | |
| 17 Mar 2000 | Third Division | H | Mansfield Town | Mansfield Town 1999–00 | 2–3 | Chris Sedgwick 35, Chris Sedgwick 69 | 5,186 |
| 21 Mar 2000 | Third Division | A | Leyton Orient | Leyton Orient 1999–00 | 1–0 | Darren Garner 58 | 3,959 |
| 25 Mar 2000 | Third Division | H | Peterborough United | Peterborough United 1999–00 | 1–1 | Paul Hurst 14 | 5,319 |
| 1 Apr 2000 | Third Division | A | Darlington | 2–2 | Guy Branston 55, Steve Tutill 59 | 7,401 | |
| 8 Apr 2000 | Third Division | H | Southend United | 0–0 | 4,327 | ||
| 15 Apr 2000 | Third Division | A | Brighton & Hove Albion | Brighton & Hove Albion 1999–00 | 1–1 | Steve Thompson 32 | 5,805 |
| 22 Apr 2000 | Third Division | A | Barnet | 0–1 | 3,239 | ||
| 24 Apr 2000 | Third Division | H | Cheltenham Town | Cheltenham Town 1999–00 | 2–0 | Darren Garner 12, Jason White 84 | 5,447 |
| 29 Apr 2000 | Third Division | A | Hartlepool United | 2–1 | Leo Fortune-West 6, Guy Branston 49 | 4,673 | |
| 6 May 2000 | Third Division | H | Swansea City | Swansea City 1999–00 | 1–1 | Lee Glover 90 | 10,863 |
77 of the goals in this season carry a named scorer.
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