Middlesbrough football club match record: 1999
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1998-99 season
| Date | Match | Result | Score | Competition |
|---|---|---|---|---|
| 15 Aug 1998 | Middlesbrough v Leeds United | D | 0-0 | Premier League |
| 23 Aug 1998 | Aston Villa v Middlesbrough | L | 3-1 | Premier League |
| 29 Aug 1998 | Middlesbrough v Derby County | D | 1-1 | Premier League |
| 09 Sep 1998 | Leicester City v Middlesbrough | W | 0-1 | Premier League |
| 13 Sep 1998 | Tottenham Hotspur v Middlesbrough | W | 0-3 | Premier League |
| 16 Sep 1998 | Middlesbrough v Wycombe Wanderers | W | 2-0 | League Cup |
| 19 Sep 1998 | Middlesbrough v Everton | D | 2-2 | Premier League |
| 22 Sep 1998 | Wycombe Wanderers v Middlesbrough | D |
1-1 Agg: 1-3 |
League Cup |
| 26 Sep 1998 | Chelsea v Middlesbrough | L | 2-0 | Premier League |
| 03 Oct 1998 | Middlesbrough v Sheffield Wednesday | W | 4-0 | Premier League |
| 17 Oct 1998 | Middlesbrough v Blackburn Rovers | W | 2-1 | Premier League |
| 24 Oct 1998 | Wimbledon v Middlesbrough | D | 2-2 | Premier League |
| 28 Oct 1998 | Middlesbrough v Everton | L | 2-3 | League Cup |
| 01 Nov 1998 | Middlesbrough v Nottingham Forest | D | 1-1 | Premier League |
| 07 Nov 1998 | Southampton v Middlesbrough | D | 3-3 | Premier League |
| 14 Nov 1998 | Charlton Athletic v Middlesbrough | D | 1-1 | Premier League |
| 21 Nov 1998 | Middlesbrough v Coventry City | W | 2-0 | Premier League |
| 29 Nov 1998 | Arsenal v Middlesbrough | D | 1-1 | Premier League |
| 06 Dec 1998 | Middlesbrough v Newcastle United | D | 2-2 | Premier League |
| 12 Dec 1998 | Middlesbrough v West Ham United | W | 1-0 | Premier League |
| 19 Dec 1998 | Manchester United v Middlesbrough | W | 2-3 | Premier League |
| 26 Dec 1998 | Middlesbrough v Liverpool | L | 1-3 | Premier League |
| 28 Dec 1998 | Derby County v Middlesbrough | L | 2-1 | Premier League |
| 03 Jan 1999 | Manchester United v Middlesbrough | L | 3-1 | FA Cup |
| 09 Jan 1999 | Middlesbrough v Aston Villa | D | 0-0 | Premier League |
| 16 Jan 1999 | Leeds United v Middlesbrough | L | 2-0 | Premier League |
| 30 Jan 1999 | Middlesbrough v Leicester City | D | 0-0 | Premier League |
| 06 Feb 1999 | Liverpool v Middlesbrough | L | 3-1 | Premier League |
| 17 Feb 1999 | Everton v Middlesbrough | L | 5-0 | Premier League |
| 20 Feb 1999 | Middlesbrough v Tottenham Hotspur | D | 0-0 | Premier League |
| 27 Feb 1999 | Sheffield Wednesday v Middlesbrough | L | 3-1 | Premier League |
| 14 Mar 1999 | Middlesbrough v Southampton | W | 3-0 | Premier League |
| 20 Mar 1999 | Nottingham Forest v Middlesbrough | W | 1-2 | Premier League |
| 03 Apr 1999 | Blackburn Rovers v Middlesbrough | D | 0-0 | Premier League |
| 05 Apr 1999 | Middlesbrough v Wimbledon | W | 3-1 | Premier League |
| 10 Apr 1999 | Middlesbrough v Charlton Athletic | W | 2-0 | Premier League |
| 14 Apr 1999 | Middlesbrough v Chelsea | D | 0-0 | Premier League |
| 17 Apr 1999 | Coventry City v Middlesbrough | W | 1-2 | Premier League |
| 24 Apr 1999 | Middlesbrough v Arsenal | L | 1-6 | Premier League |
| 01 May 1999 | Newcastle United v Middlesbrough | D | 1-1 | Premier League |
| 09 May 1999 | Middlesbrough v Manchester United | L | 0-1 | Premier League |
| 16 May 1999 | West Ham United v Middlesbrough | L | 4-0 | Premier League |