Every competitive match Swindon Town played in 1999–00, in First Division — 49 matches, 8 won, 13 drawn, 28 lost, with scorers and attendances where the record holds them.
| Date | Competition | Venue | Opponent | Their season | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 7 Aug 1999 | First Division | A | Walsall | Walsall 1999–00 | 0–0 | 6,437 | |
| 10 Aug 1999 | League Cup | H | Leyton Orient | Leyton Orient 1999–00 | 0–1 | 3,587 | |
| 15 Aug 1999 | First Division | H | Ipswich Town | Ipswich Town 1999–00 | 1–4 | Giuliano Grazioli | 6,195 |
| 21 Aug 1999 | First Division | A | Crystal Palace | Crystal Palace 1999–00 | 2–1 | Giuliano Grazioli, Iffy Onoura | 12,726 |
| 24 Aug 1999 | League Cup | A | Leyton Orient | Leyton Orient 1999–00 | 1–1 | Mark Walters | 4,000 |
| 28 Aug 1999 | First Division | H | West Bromwich Albion | West Bromwich Albion 1999–00 | 1–2 | Mark Walters | 6,565 |
| 30 Aug 1999 | First Division | A | Grimsby Town | Grimsby Town 1999–00 | 0–1 | 5,705 | |
| 11 Sep 1999 | First Division | H | Nottingham Forest | Nottingham Forest 1999–00 | 0–0 | 8,203 | |
| 18 Sep 1999 | First Division | A | Crewe Alexandra | Crewe Alexandra 1999–00 | 1–2 | George Ndah | 5,280 |
| 25 Sep 1999 | First Division | A | Port Vale | Port Vale 1999–00 | 0–2 | 4,629 | |
| 28 Sep 1999 | First Division | H | Blackburn Rovers | Blackburn Rovers 1999–00 | 2–1 | Simon Grayson, Bobby Howe | 7,354 |
| 2 Oct 1999 | First Division | H | Bolton Wanderers | Bolton Wanderers 1999–00 | 0–4 | 6,711 | |
| 9 Oct 1999 | First Division | H | Stockport County | Stockport County 1999–00 | 1–1 | Chris Hay | 5,318 |
| 16 Oct 1999 | First Division | A | Fulham | Fulham 1999–00 | 0–1 | 13,715 | |
| 19 Oct 1999 | First Division | A | Barnsley | Barnsley 1999–00 | 0–1 | 12,026 | |
| 23 Oct 1999 | First Division | H | Sheffield United | Sheffield United 1999–00 | 2–2 | Chris Hay, Chris Hay | 5,504 |
| 26 Oct 1999 | First Division | H | Port Vale | Port Vale 1999–00 | 2–1 | Iffy Onoura, Giuliano Grazioli | 5,703 |
| 30 Oct 1999 | First Division | A | Bolton Wanderers | Bolton Wanderers 1999–00 | 0–2 | 12,486 | |
| 6 Nov 1999 | First Division | A | Huddersfield Town | Huddersfield Town 1999–00 | 0–4 | 11,891 | |
| 12 Nov 1999 | First Division | H | Norwich City | Norwich City 1999–00 | 0–0 | 7,404 | |
| 20 Nov 1999 | First Division | A | Wolverhampton Wanderers | Wolverhampton Wanderers 1999–00 | 1–1 | Iffy Onoura | 19,917 |
| 23 Nov 1999 | First Division | H | Charlton Athletic | Charlton Athletic 1999–00 | 1–2 | Michael Carrick | 6,515 |
| 27 Nov 1999 | First Division | A | Birmingham City | Birmingham City 1999–00 | 1–1 | Iffy Onoura | 22,620 |
| 4 Dec 1999 | First Division | H | Walsall | Walsall 1999–00 | 1–1 | Michael Carrick | 7,186 |
| 11 Dec 1999 | FA Cup | A | Charlton Athletic | Charlton Athletic 1999–00 | 1–2 | Ty Gooden | 10,939 |
| 18 Dec 1999 | First Division | A | Manchester City | Manchester City 1999–00 | 0–3 | 31,751 | |
| 26 Dec 1999 | First Division | H | Portsmouth | Portsmouth 1999–00 | 1–1 | Chris Hay | 10,279 |
| 28 Dec 1999 | First Division | A | Tranmere Rovers | Tranmere Rovers 1999–00 | 1–3 | Chris Hay | 8,068 |
| 3 Jan 2000 | First Division | H | Queens Park Rangers | Queens Park Rangers 1999–00 | 0–1 | 9,460 | |
| 15 Jan 2000 | First Division | A | Ipswich Town | Ipswich Town 1999–00 | 0–3 | 17,326 | |
| 21 Jan 2000 | First Division | H | Crystal Palace | Crystal Palace 1999–00 | 2–4 | Alan Reeves, Gareth Hall | 5,214 |
| 29 Jan 2000 | First Division | A | West Bromwich Albion | West Bromwich Albion 1999–00 | 1–1 | Gareth Hall | 11,856 |
| 5 Feb 2000 | First Division | H | Grimsby Town | Grimsby Town 1999–00 | 0–1 | 5,784 | |
| 12 Feb 2000 | First Division | A | Blackburn Rovers | Blackburn Rovers 1999–00 | 0–0 | 16,938 | |
| 19 Feb 2000 | First Division | H | Birmingham City | Birmingham City 1999–00 | 1–4 | Chris Hay | 7,591 |
| 26 Feb 2000 | First Division | H | Crewe Alexandra | Crewe Alexandra 1999–00 | 0–1 | 5,003 | |
| 4 Mar 2000 | First Division | A | Nottingham Forest | Nottingham Forest 1999–00 | 1–3 | Chris Hay | 19,748 |
| 7 Mar 2000 | First Division | H | Huddersfield Town | Huddersfield Town 1999–00 | 2–0 | Lee Collins, Chris Hay | 4,701 |
| 11 Mar 2000 | First Division | A | Charlton Athletic | Charlton Athletic 1999–00 | 1–0 | Dean Kiely | 19,569 |
| 18 Mar 2000 | First Division | H | Wolverhampton Wanderers | Wolverhampton Wanderers 1999–00 | 1–2 | Andy Williams | 8,748 |
| 22 Mar 2000 | First Division | A | Norwich City | Norwich City 1999–00 | 2–0 | Chris Hay, Chris Hay | 13,662 |
| 25 Mar 2000 | First Division | A | Portsmouth | Portsmouth 1999–00 | 1–4 | Wayne Gray | 15,305 |
| 1 Apr 2000 | First Division | H | Manchester City | Manchester City 1999–00 | 0–2 | 12,397 | |
| 8 Apr 2000 | First Division | A | Queens Park Rangers | Queens Park Rangers 1999–00 | 1–2 | Giuliano Grazioli | 12,633 |
| 15 Apr 2000 | First Division | H | Tranmere Rovers | Tranmere Rovers 1999–00 | 3–1 | Charlie Griffin, Giuliano Grazioli, Wayne Gray | 4,925 |
| 22 Apr 2000 | First Division | H | Fulham | Fulham 1999–00 | 1–0 | Giuliano Grazioli | 7,556 |
| 24 Apr 2000 | First Division | A | Stockport County | Stockport County 1999–00 | 0–3 | 5,362 | |
| 29 Apr 2000 | First Division | H | Barnsley | Barnsley 1999–00 | 1–2 | Jonny Williams | 6,151 |
| 7 May 2000 | First Division | A | Sheffield United | Sheffield United 1999–00 | 2–2 | Giuliano Grazioli, Giuliano Grazioli | 12,603 |
40 of the goals in this season carry a named scorer.
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