Every competitive match Hull City played in 1999–00, in Third Division — 58 matches, 21 won, 17 drawn, 20 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 | Exeter City | Exeter City 1999–00 | 0–1 | 3,834 | |
| 10 Aug 1999 | League Cup | A | Rotherham United | Rotherham United 1999–00 | 1–0 | John Eyre 18 | 3,294 |
| 14 Aug 1999 | Third Division | H | Lincoln City | Lincoln City 1999–00 | 1–1 | Mark Greaves 28 | 7,046 |
| 21 Aug 1999 | Third Division | A | Cheltenham | Cheltenham 1999–00 | 0–1 | 4,427 | |
| 24 Aug 1999 | League Cup | H | Rotherham United | Rotherham United 1999–00 | 2–0 | Colin Alcide 10, David Brown 73 | 4,373 |
| 28 Aug 1999 | Third Division | H | Macclesfield Town | 2–3 | Colin Alcide 13, David Brown 64 | 6,222 | |
| 31 Aug 1999 | Third Division | A | Brighton & Hove Albion | Brighton & Hove Albion 1999–00 | 0–3 | 5,856 | |
| 3 Sep 1999 | Third Division | H | Chester | 2–1 | John Eyre 35, John Eyre 77 | 6,167 | |
| 11 Sep 1999 | Third Division | A | Torquay United | 1–0 | John Eyre 33 | 2,446 | |
| 14 Sep 1999 | League Cup | H | Liverpool | Liverpool 1999–00 | 1–5 | David Brown 58 | 10,034 |
| 18 Sep 1999 | Third Division | H | Swansea City | Swansea City 1999–00 | 2–0 | David Brown 39, Jamie Wood 56 | 5,871 |
| 21 Sep 1999 | League Cup | A | Liverpool | Liverpool 1999–00 | 2–4 | John Eyre 51, Colin Alcide 56 | 24,318 |
| 25 Sep 1999 | Third Division | H | York City | 1–1 | John Eyre 22 | 8,293 | |
| 2 Oct 1999 | Third Division | A | Barnet | 0–0 | 3,449 | ||
| 9 Oct 1999 | Third Division | A | Hartlepool United | 0–2 | 3,114 | ||
| 16 Oct 1999 | Third Division | H | Northampton Town | Northampton Town 1999–00 | 0–1 | 6,467 | |
| 19 Oct 1999 | Third Division | H | Plymouth Argyle | Plymouth Argyle 1999–00 | 0–1 | 4,727 | |
| 23 Oct 1999 | Third Division | A | York City | 1–1 | Gareth Williams 67 | 5,109 | |
| 30 Oct 1999 | FA Cup | A | Macclesfield Town | 0–0 | 2,404 | ||
| 2 Nov 1999 | Third Division | A | Rochdale | Rochdale 1999–00 | 2–0 | Steve Harper 8, Theodore Whitmore 90 | 2,265 |
| 6 Nov 1999 | Third Division | H | Rotherham United | Rotherham United 1999–00 | 0–0 | 7,045 | |
| 9 Nov 1999 | FA Cup | H | Macclesfield Town | 4–0 | John Eyre 3, Mark Greaves 7, David Brown 29, John Eyre 61 | 4,844 | |
| 12 Nov 1999 | Third Division | A | Southend United | 2–1 | Mark Greaves 74, Gary Brabin 82 | 4,940 | |
| 20 Nov 1999 | FA Cup | A | Hayes | 2–2 | Roddins 4, Mike Edwards 56 | 2,749 | |
| 23 Nov 1999 | Third Division | H | Halifax Town | 0–1 | 6,067 | ||
| 27 Nov 1999 | Third Division | A | Shrewsbury Town | Shrewsbury Town 1999–00 | 0–3 | 2,577 | |
| 30 Nov 1999 | FA Cup | H | Hayes | 3–2 | David Brown 49, Mike Edwards 97, Jamie Wood 112 | 7,000 | |
| 4 Dec 1999 | Third Division | H | Exeter City | Exeter City 1999–00 | 4–0 | Mike Edwards 22, Steve Harper 45, Steve Harper 75, Steve Harper 89 | 5,683 |
| 7 Dec 1999 | EFL Trophy | A | York City | 1–0 | Steve Morgan 20 | 1,005 | |
| 11 Dec 1999 | FA Cup | H | Chelsea | Chelsea 1999–00 | 1–6 | David Brown 38 | 10,279 |
| 18 Dec 1999 | Third Division | H | Carlisle United | Carlisle United 1999–00 | 2–1 | Jamie Wood 75, John Eyre 87 | 4,727 |
| 26 Dec 1999 | Third Division | A | Darlington | 0–0 | 7,058 | ||
| 28 Dec 1999 | Third Division | H | Mansfield Town | Mansfield Town 1999–00 | 2–0 | Mark Greaves 37, Warren Joyce 37 | 7,215 |
| 3 Jan 2000 | Third Division | A | Leyton Orient | Leyton Orient 1999–00 | 0–0 | 5,169 | |
| 8 Jan 2000 | Third Division | H | Peterborough United | Peterborough United 1999–00 | 2–3 | David Brown 43, John Eyre 55 | 5,898 |
| 11 Jan 2000 | EFL Trophy | H | Chester | 2–0 | Warren Joyce 33, Steve Morgan 76 | 1,680 | |
| 15 Jan 2000 | Third Division | A | Lincoln City | Lincoln City 1999–00 | 1–2 | David Brown 83 | 4,687 |
| 22 Jan 2000 | Third Division | H | Cheltenham | Cheltenham 1999–00 | 1–1 | Theodore Whitmore 1 | 4,691 |
| 25 Jan 2000 | EFL Trophy | A | Rochdale | Rochdale 1999–00 | 0–0 | 1,742 | |
| 29 Jan 2000 | Third Division | A | Macclesfield Town | 2–0 | John Eyre 47, John Eyre 54 | 1,900 | |
| 5 Feb 2000 | Third Division | H | Brighton & Hove Albion | Brighton & Hove Albion 1999–00 | 2–0 | Jason Harris 66, Jason Harris 82 | 5,167 |
| 12 Feb 2000 | Third Division | A | Chester | 0–0 | 2,802 | ||
| 19 Feb 2000 | Third Division | H | Shrewsbury Town | Shrewsbury Town 1999–00 | 0–0 | 5,100 | |
| 22 Feb 2000 | Third Division | A | Peterborough United | Peterborough United 1999–00 | 1–2 | Gary Brabin 48 | 6,668 |
| 26 Feb 2000 | Third Division | A | Swansea City | Swansea City 1999–00 | 0–0 | 6,137 | |
| 4 Mar 2000 | Third Division | H | Torquay United | 0–0 | 4,668 | ||
| 7 Mar 2000 | Third Division | A | Rotherham United | Rotherham United 1999–00 | 0–3 | 4,881 | |
| 11 Mar 2000 | Third Division | H | Rochdale | Rochdale 1999–00 | 2–2 | Jamie Wood 25, Jamie Wood 81 | 4,219 |
| 18 Mar 2000 | Third Division | A | Halifax Town | 1–0 | Jamie Wood 77 | 2,519 | |
| 21 Mar 2000 | Third Division | H | Southend United | 0–0 | 4,150 | ||
| 25 Mar 2000 | Third Division | H | Darlington | 0–1 | 5,617 | ||
| 1 Apr 2000 | Third Division | A | Carlisle United | Carlisle United 1999–00 | 4–0 | Richard Prokas 32, Jason Harris 45, Jason Harris 77, Steve Morgan 80 | 3,495 |
| 8 Apr 2000 | Third Division | H | Leyton Orient | Leyton Orient 1999–00 | 2–0 | Jon Whitney 13, David Brown 90 | 4,422 |
| 15 Apr 2000 | Third Division | A | Mansfield Town | Mansfield Town 1999–00 | 1–0 | David Brown 83 | 2,213 |
| 21 Apr 2000 | Third Division | A | Northampton Town | Northampton Town 1999–00 | 0–1 | 6,758 | |
| 24 Apr 2000 | Third Division | H | Barnet | 1–3 | Gary Brabin 49 | 4,883 | |
| 29 Apr 2000 | Third Division | A | Plymouth Argyle | Plymouth Argyle 1999–00 | 1–0 | Jamie Wood 21 | 4,233 |
| 6 May 2000 | Third Division | H | Hartlepool United | 0–3 | 7,620 |
62 of the goals in this season carry a named scorer.
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