Every competitive match Sheffield United played in 1999–00, in First Division — 53 matches, 16 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 | First Division | A | Portsmouth | Portsmouth 1999–00 | 0–2 | 17,667 | |
| 10 Aug 1999 | League Cup | H | Shrewsbury Town | Shrewsbury Town 1999–00 | 3–0 | Pyotr Kachura, Martin Smith, Martin Smith | 6,419 |
| 14 Aug 1999 | First Division | H | Walsall | Walsall 1999–00 | 1–1 | Shaun Murphy | 12,581 |
| 21 Aug 1999 | First Division | A | Manchester City | Manchester City 1999–00 | 0–6 | 30,110 | |
| 24 Aug 1999 | League Cup | A | Shrewsbury Town | Shrewsbury Town 1999–00 | 3–0 | Marcelo dos Santos Cipriano, Marcelo dos Santos Cipriano, Martin Smith | 1,723 |
| 28 Aug 1999 | First Division | H | Ipswich Town | Ipswich Town 1999–00 | 2–2 | Martin Smith, Marcelo dos Santos Cipriano | 12,455 |
| 30 Aug 1999 | First Division | A | Tranmere Rovers | Tranmere Rovers 1999–00 | 3–1 | Paul Devlin, Paul Devlin, Martin Smith | 5,436 |
| 4 Sep 1999 | First Division | H | Crystal Palace | Crystal Palace 1999–00 | 3–1 | Marcelo dos Santos Cipriano, Marcelo dos Santos Cipriano, Bobby Ford | 11,886 |
| 14 Sep 1999 | League Cup | H | Preston North End | Preston North End 1999–00 | 2–0 | Martin Smith, Pyotr Kachura | 5,350 |
| 18 Sep 1999 | First Division | H | Charlton Athletic | Charlton Athletic 1999–00 | 1–2 | Pyotr Kachura | 13,216 |
| 21 Sep 1999 | League Cup | A | Preston North End | Preston North End 1999–00 | 0–3 | 5,658 | |
| 25 Sep 1999 | First Division | H | Wolverhampton Wanderers | Wolverhampton Wanderers 1999–00 | 3–0 | Martin Smith, Martin Smith, Paul Devlin | 14,163 |
| 2 Oct 1999 | First Division | A | Huddersfield Town | Huddersfield Town 1999–00 | 1–4 | Shaun Murphy | 14,238 |
| 9 Oct 1999 | First Division | A | Crewe Alexandra | Crewe Alexandra 1999–00 | 0–1 | 5,304 | |
| 16 Oct 1999 | First Division | H | Nottingham Forest | Nottingham Forest 1999–00 | 2–1 | Martin Smith, Martin Smith | 15,687 |
| 19 Oct 1999 | First Division | H | Norwich City | Norwich City 1999–00 | 0–0 | 11,907 | |
| 23 Oct 1999 | First Division | A | Swindon Town | Swindon Town 1999–00 | 2–2 | Martin Smith, Martin Smith | 5,504 |
| 26 Oct 1999 | First Division | A | Wolverhampton Wanderers | Wolverhampton Wanderers 1999–00 | 0–1 | 24,402 | |
| 30 Oct 1999 | First Division | H | Huddersfield Town | Huddersfield Town 1999–00 | 0–1 | 14,928 | |
| 6 Nov 1999 | First Division | A | Barnsley | Barnsley 1999–00 | 0–2 | 16,301 | |
| 14 Nov 1999 | First Division | H | Bolton Wanderers | Bolton Wanderers 1999–00 | 1–2 | Marcus Bent | 10,013 |
| 20 Nov 1999 | First Division | A | Stockport County | Stockport County 1999–00 | 1–1 | Marcus Bent | 6,614 |
| 23 Nov 1999 | First Division | H | Port Vale | Port Vale 1999–00 | 1–3 | Lee Sandford | 8,965 |
| 27 Nov 1999 | First Division | A | West Bromwich Albion | West Bromwich Albion 1999–00 | 2–2 | Martin Smith, Bruno Ribeiro | 12,278 |
| 30 Nov 1999 | First Division | A | Queens Park Rangers | Queens Park Rangers 1999–00 | 1–3 | Paul Devlin | 9,922 |
| 4 Dec 1999 | First Division | H | Portsmouth | Portsmouth 1999–00 | 1–0 | Paul Devlin | 10,834 |
| 12 Dec 1999 | FA Cup | H | Rushden & Diamonds | 1–1 | Marcus Bent | 10,104 | |
| 19 Dec 1999 | First Division | H | Blackburn Rovers | Blackburn Rovers 1999–00 | 2–1 | Marcus Bent, Marcus Bent | 10,437 |
| 21 Dec 1999 | FA Cup | A | Rushden & Diamonds | 1–1 | Shaun Derry | 6,010 | |
| 26 Dec 1999 | First Division | A | Birmingham City | Birmingham City 1999–00 | 2–0 | Paul Devlin, Martin Smith | 22,874 |
| 28 Dec 1999 | First Division | H | Fulham | Fulham 1999–00 | 2–0 | Paul Devlin, Marcus Bent | 17,375 |
| 3 Jan 2000 | First Division | A | Grimsby Town | Grimsby Town 1999–00 | 2–2 | Marcus Bent, Paul Hall | 7,618 |
| 8 Jan 2000 | FA Cup | A | Newcastle United | Newcastle United 1999–00 | 1–4 | Martin Smith | 36,220 |
| 15 Jan 2000 | First Division | A | Walsall | Walsall 1999–00 | 1–2 | Paul Devlin | 6,222 |
| 22 Jan 2000 | First Division | H | Manchester City | Manchester City 1999–00 | 1–0 | Michael Brown | 23,862 |
| 29 Jan 2000 | First Division | A | Ipswich Town | Ipswich Town 1999–00 | 1–1 | Marcus Bent | 17,350 |
| 5 Feb 2000 | First Division | H | Tranmere Rovers | Tranmere Rovers 1999–00 | 3–1 | Paul Devlin, Marcus Bent, Bobby Ford | 14,219 |
| 12 Feb 2000 | First Division | A | Crystal Palace | Crystal Palace 1999–00 | 1–1 | Marcus Bent | 14,877 |
| 19 Feb 2000 | First Division | H | West Bromwich Albion | West Bromwich Albion 1999–00 | 6–0 | Marcus Bent, Marcus Bent, Marcus Bent, Paul Devlin, Alex Notman, Michael Brown | 14,519 |
| 26 Feb 2000 | First Division | A | Charlton Athletic | Charlton Athletic 1999–00 | 0–1 | 19,249 | |
| 5 Mar 2000 | First Division | H | Queens Park Rangers | Queens Park Rangers 1999–00 | 1–1 | Alex Notman | 11,554 |
| 7 Mar 2000 | First Division | H | Barnsley | Barnsley 1999–00 | 3–3 | Alex Notman, Michael Brown, Marcus Bent | 22,376 |
| 11 Mar 2000 | First Division | A | Port Vale | Port Vale 1999–00 | 3–2 | Marcus Bent, Curtis Woodhouse, Laurent D'Jaffo | 5,484 |
| 18 Mar 2000 | First Division | H | Stockport County | Stockport County 1999–00 | 1–0 | Curtis Woodhouse | 14,907 |
| 21 Mar 2000 | First Division | A | Bolton Wanderers | Bolton Wanderers 1999–00 | 0–2 | 11,891 | |
| 25 Mar 2000 | First Division | H | Birmingham City | Birmingham City 1999–00 | 1–2 | Marcus Bent | 15,486 |
| 1 Apr 2000 | First Division | A | Blackburn Rovers | Blackburn Rovers 1999–00 | 0–5 | 17,769 | |
| 8 Apr 2000 | First Division | H | Grimsby Town | Grimsby Town 1999–00 | 0–0 | 11,612 | |
| 15 Apr 2000 | First Division | A | Fulham | Fulham 1999–00 | 0–4 | 12,197 | |
| 22 Apr 2000 | First Division | A | Nottingham Forest | Nottingham Forest 1999–00 | 0–0 | 17,172 | |
| 24 Apr 2000 | First Division | H | Crewe Alexandra | Crewe Alexandra 1999–00 | 1–1 | Curtis Woodhouse | 9,923 |
| 29 Apr 2000 | First Division | A | Norwich City | Norwich City 1999–00 | 1–2 | Paul Devlin | 16,921 |
| 7 May 2000 | First Division | H | Swindon Town | Swindon Town 1999–00 | 2–2 | Wayne Quinn, Adam Burley | 12,603 |
70 of the goals in this season carry a named scorer.
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