Middlesbrough football club match record: 2000
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1999-00 season
| Date | Match | Result | Score | Competition |
|---|---|---|---|---|
| 07 Aug 1999 | Middlesbrough v Bradford City | L | 0-1 | Premier League |
| 10 Aug 1999 | Wimbledon v Middlesbrough | W | 2-3 | Premier League |
| 14 Aug 1999 | Derby County v Middlesbrough | W | 1-3 | Premier League |
| 21 Aug 1999 | Middlesbrough v Liverpool | W | 1-0 | Premier League |
| 24 Aug 1999 | Middlesbrough v Leicester City | L | 0-3 | Premier League |
| 28 Aug 1999 | Aston Villa v Middlesbrough | L | 1-0 | Premier League |
| 11 Sep 1999 | Middlesbrough v Southampton | W | 3-2 | Premier League |
| 14 Sep 1999 | Chesterfield v Middlesbrough | D | 0-0 | League Cup |
| 19 Sep 1999 | Leeds United v Middlesbrough | L | 2-0 | Premier League |
| 21 Sep 1999 | Middlesbrough v Chesterfield | W |
2-1 Agg: 2-1 |
League Cup |
| 25 Sep 1999 | Middlesbrough v Chelsea | L | 0-1 | Premier League |
| 03 Oct 1999 | Newcastle United v Middlesbrough | L | 2-1 | Premier League |
| 13 Oct 1999 | Middlesbrough v Watford | W | 1-0 | League Cup |
| 17 Oct 1999 | Middlesbrough v West Ham United | W | 2-0 | Premier League |
| 24 Oct 1999 | Watford v Middlesbrough | W | 1-3 | Premier League |
| 30 Oct 1999 | Middlesbrough v Everton | W | 2-1 | Premier League |
| 06 Nov 1999 | Middlesbrough v Sunderland | D | 1-1 | Premier League |
| 20 Nov 1999 | Arsenal v Middlesbrough | L | 5-1 | Premier League |
| 27 Nov 1999 | Middlesbrough v Wimbledon | D | 0-0 | Premier League |
| 30 Nov 1999 | Middlesbrough v Arsenal | W | 2-2 (3-1) | League Cup |
| 04 Dec 1999 | Bradford City v Middlesbrough | D | 1-1 | Premier League |
| 11 Dec 1999 | Wrexham v Middlesbrough | L | 2-1 | FA Cup |
| 14 Dec 1999 | Tranmere Rovers v Middlesbrough | L | 2-1 | League Cup |
| 18 Dec 1999 | Middlesbrough v Tottenham Hotspur | W | 2-1 | Premier League |
| 26 Dec 1999 | Sheffield Wednesday v Middlesbrough | L | 1-0 | Premier League |
| 15 Jan 2000 | Middlesbrough v Derby County | L | 1-4 | Premier League |
| 22 Jan 2000 | Liverpool v Middlesbrough | D | 0-0 | Premier League |
| 29 Jan 2000 | Manchester United v Middlesbrough | L | 1-0 | Premier League |
| 05 Feb 2000 | Leicester City v Middlesbrough | L | 2-1 | Premier League |
| 14 Feb 2000 | Middlesbrough v Aston Villa | L | 0-4 | Premier League |
| 19 Feb 2000 | Middlesbrough v Coventry City | W | 2-0 | Premier League |
| 26 Feb 2000 | Middlesbrough v Leeds United | D | 0-0 | Premier League |
| 04 Mar 2000 | Southampton v Middlesbrough | D | 1-1 | Premier League |
| 12 Mar 2000 | Middlesbrough v Arsenal | W | 2-1 | Premier League |
| 18 Mar 2000 | Sunderland v Middlesbrough | D | 1-1 | Premier League |
| 25 Mar 2000 | Middlesbrough v Sheffield Wednesday | W | 1-0 | Premier League |
| 03 Apr 2000 | Tottenham Hotspur v Middlesbrough | W | 2-3 | Premier League |
| 10 Apr 2000 | Middlesbrough v Manchester United | L | 3-4 | Premier League |
| 15 Apr 2000 | Coventry City v Middlesbrough | L | 2-1 | Premier League |
| 22 Apr 2000 | Chelsea v Middlesbrough | D | 1-1 | Premier League |
| 29 Apr 2000 | West Ham United v Middlesbrough | W | 0-1 | Premier League |
| 02 May 2000 | Middlesbrough v Newcastle United | D | 2-2 | Premier League |
| 06 May 2000 | Middlesbrough v Watford | D | 1-1 | Premier League |
| 14 May 2000 | Everton v Middlesbrough | W | 0-2 | Premier League |