Every competitive match Birmingham City played in 1999–00, in First Division — 56 matches, 29 won, 11 drawn, 16 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 | Fulham | Fulham 1999–00 | 2–2 | Bryan Hughes 62, Stan Lazaridis 85 | 24,042 |
| 10 Aug 1999 | League Cup | H | Exeter City | Exeter City 1999–00 | 3–0 | A. Johnson 17, Jon Richardson 42, Dele Adebola 75 | 18,976 |
| 14 Aug 1999 | First Division | A | Norwich City | Norwich City 1999–00 | 1–0 | Jon McCarthy 11 | 15,261 |
| 21 Aug 1999 | First Division | H | Port Vale | Port Vale 1999–00 | 4–2 | Hughes 8, Paul Furlong 18, Paul Furlong 34, Hughes 51 | 18,089 |
| 24 Aug 1999 | League Cup | A | Exeter City | Exeter City 1999–00 | 2–1 | Richardson 22, Martin O'Connor 50 | 2,338 |
| 27 Aug 1999 | First Division | A | Stockport County | Stockport County 1999–00 | 0–2 | 6,115 | |
| 30 Aug 1999 | First Division | H | Crewe Alexandra | Crewe Alexandra 1999–00 | 5–1 | M. Johnson 12, McCarthy 20, Furlong 30, David Holdsworth 52, Peter Ndlovu 77 | 24,085 |
| 5 Sep 1999 | First Division | A | Bolton Wanderers | Bolton Wanderers 1999–00 | 3–3 | Holdsworth 26, Furlong 37, Furlong 45 | 11,668 |
| 11 Sep 1999 | First Division | H | West Bromwich Albion | West Bromwich Albion 1999–00 | 1–1 | A. Johnson 43 | 25,945 |
| 14 Sep 1999 | League Cup | H | Bristol Rovers | Bristol Rovers 1999–00 | 2–0 | O'Connor 51, David Holdsworth 67 | 17,457 |
| 18 Sep 1999 | First Division | A | Ipswich Town | Ipswich Town 1999–00 | 1–0 | Furlong 10 | 19,758 |
| 21 Sep 1999 | League Cup | A | Bristol Rovers | Bristol Rovers 1999–00 | 1–0 | Gary Rowett 48 | 5,456 |
| 25 Sep 1999 | First Division | H | Queens Park Rangers | Queens Park Rangers 1999–00 | 2–0 | Furlong 44, Penalty kick | 18,748 |
| 2 Oct 1999 | First Division | A | Charlton Athletic | Charlton Athletic 1999–00 | 0–1 | 19,753 | |
| 8 Oct 1999 | First Division | A | Walsall | Walsall 1999–00 | 0–1 | 7,164 | |
| 12 Oct 1999 | League Cup | H | Newcastle United | Newcastle United 1999–00 | 2–0 | O'Connor 45, Darren Purse 60 | 19,795 |
| 16 Oct 1999 | First Division | H | Crystal Palace | Crystal Palace 1999–00 | 2–0 | Darren Purse 10, McCarthy 48 | 21,582 |
| 19 Oct 1999 | First Division | H | Manchester City | Manchester City 1999–00 | 0–1 | 22,126 | |
| 23 Oct 1999 | First Division | A | Grimsby Town | Grimsby Town 1999–00 | 1–1 | Christopher Wreh 37 | 6,266 |
| 27 Oct 1999 | First Division | A | Queens Park Rangers | Queens Park Rangers 1999–00 | 2–2 | Marcelo dos Santos Cipriano 74, Marcelo dos Santos Cipriano 76 | 11,196 |
| 30 Oct 1999 | First Division | H | Charlton Athletic | Charlton Athletic 1999–00 | 1–0 | Hughes 25 | 19,172 |
| 6 Nov 1999 | First Division | A | Portsmouth | Portsmouth 1999–00 | 2–2 | Lazaridis 59, M. Johnson 62 | 12,756 |
| 20 Nov 1999 | First Division | A | Barnsley | Barnsley 1999–00 | 1–2 | McCarthy 70 | 14,520 |
| 23 Nov 1999 | First Division | H | Tranmere Rovers | Tranmere Rovers 1999–00 | 3–1 | Martin Grainger 2, Marcelo 27, Graham Hyde 45 | 21,132 |
| 27 Nov 1999 | First Division | H | Swindon Town | Swindon Town 1999–00 | 1–1 | Grainger 26 | 22,620 |
| 30 Nov 1999 | League Cup | H | West Ham United | West Ham United 1999–00 | 2–3 | Graham Hyde 8, Martin Grainger 44 | 17,728 |
| 4 Dec 1999 | First Division | A | Fulham | Fulham 1999–00 | 0–0 | 12,290 | |
| 11 Dec 1999 | FA Cup | A | Watford | Watford 1999–00 | 1–0 | Gary Rowett 66 | 8,144 |
| 17 Dec 1999 | First Division | A | Wolverhampton Wanderers | Wolverhampton Wanderers 1999–00 | 1–2 | Hughes 15 | 19,724 |
| 26 Dec 1999 | First Division | H | Sheffield United | Sheffield United 1999–00 | 0–2 | 22,874 | |
| 28 Dec 1999 | First Division | A | Nottingham Forest | Nottingham Forest 1999–00 | 0–1 | 20,821 | |
| 3 Jan 2000 | First Division | H | Huddersfield Town | Huddersfield Town 1999–00 | 1–0 | Hughes 1 | 19,558 |
| 8 Jan 2000 | FA Cup | A | Everton | Everton 1999–00 | 0–2 | 25,405 | |
| 15 Jan 2000 | First Division | H | Norwich City | Norwich City 1999–00 | 2–0 | Grainger 16, Grainger 30 | 21,007 |
| 22 Jan 2000 | First Division | A | Port Vale | Port Vale 1999–00 | 1–3 | Hughes 48 | 7,702 |
| 29 Jan 2000 | First Division | H | Stockport County | Stockport County 1999–00 | 2–1 | Holdsworth 62, Hughes 72 | 17,150 |
| 5 Feb 2000 | First Division | A | Crewe Alexandra | Crewe Alexandra 1999–00 | 3–2 | Martin O'Connor 45, Hughes 54, Adebola 70 | 6,289 |
| 12 Feb 2000 | First Division | H | Bolton Wanderers | Bolton Wanderers 1999–00 | 2–1 | Isaiah Rankin 50, Adebola 66 | 18,426 |
| 15 Feb 2000 | First Division | H | Blackburn Rovers | Blackburn Rovers 1999–00 | 1–0 | O'Connor 33 | 20,719 |
| 19 Feb 2000 | First Division | A | Swindon Town | Swindon Town 1999–00 | 4–1 | Purse 11, Rankin 21, Adebola 26, Grainger 74 | 7,591 |
| 27 Feb 2000 | First Division | H | Ipswich Town | Ipswich Town 1999–00 | 1–1 | Tony Mowbray 17 | 20,493 |
| 4 Mar 2000 | First Division | A | West Bromwich Albion | West Bromwich Albion 1999–00 | 3–0 | Adebola 6, Adebola 8, Marcelo 86 | 17,029 |
| 7 Mar 2000 | First Division | H | Portsmouth | Portsmouth 1999–00 | 1–0 | Marcelo 49 | 19,573 |
| 11 Mar 2000 | First Division | A | Tranmere Rovers | Tranmere Rovers 1999–00 | 1–2 | Gary Rowett 45 | 9,232 |
| 18 Mar 2000 | First Division | H | Barnsley | Barnsley 1999–00 | 3–1 | Rankin 25, Holdsworth 45, Rankin 63 | 25,108 |
| 22 Mar 2000 | First Division | A | Blackburn Rovers | Blackburn Rovers 1999–00 | 0–1 | 18,096 | |
| 25 Mar 2000 | First Division | A | Sheffield United | Sheffield United 1999–00 | 2–1 | Rob Kozluk 52, Hughes 54 | 15,486 |
| 1 Apr 2000 | First Division | H | Wolverhampton Wanderers | Wolverhampton Wanderers 1999–00 | 1–0 | Holdsworth 53 | 29,050 |
| 8 Apr 2000 | First Division | A | Huddersfield Town | Huddersfield Town 1999–00 | 0–0 | 16,961 | |
| 15 Apr 2000 | First Division | H | Nottingham Forest | Nottingham Forest 1999–00 | 0–1 | 23,006 | |
| 22 Apr 2000 | First Division | A | Crystal Palace | Crystal Palace 1999–00 | 2–0 | Dean Austin 45, Furlong 61 | 17,144 |
| 24 Apr 2000 | First Division | H | Walsall | Walsall 1999–00 | 2–0 | Furlong 70, Furlong 90 | 24,268 |
| 28 Apr 2000 | First Division | A | Manchester City | Manchester City 1999–00 | 0–1 | 32,062 | |
| 7 May 2000 | First Division | H | Grimsby Town | Grimsby Town 1999–00 | 0–0 | 25,263 | |
| 13 May 2000 | Play-offs | H | Barnsley | Barnsley 1999–00 | 0–4 | 26,492 | |
| 18 May 2000 | Play-offs | A | Barnsley | Barnsley 1999–00 | 2–1 | Gary Rowett 33, Marcelo dos Santos Cipriano 75 | 19,050 |
80 of the goals in this season carry a named scorer.
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