Every competitive match Middlesbrough played in 1998–99, in Premier League — 42 matches, 13 won, 16 drawn, 13 lost, with scorers and attendances where the record holds them.
| Date | Competition | Venue | Opponent | Their season | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 15 Aug 1998 | Premier League | H | Leeds United | Leeds United 1998–99 | 0–0 | 34,162 | |
| 23 Aug 1998 | Premier League | A | Aston Villa | Aston Villa 1998–99 | 1–3 | Mikkel Beck | 29,559 |
| 29 Aug 1998 | Premier League | H | Derby County | Derby County 1998–99 | 1–1 | Hamilton Ricard | 34,121 |
| 9 Sep 1998 | Premier League | A | Leicester City | Leicester City 1998–99 | 1–0 | Paul Gascoigne | 20,635 |
| 13 Sep 1998 | Premier League | A | Tottenham Hotspur | Tottenham Hotspur 1998–99 | 3–0 | Hamilton Ricard, Hamilton Ricard, Vladimír Kinder | 30,437 |
| 16 Sep 1998 | League Cup | H | Wycombe Wanderers | Wycombe Wanderers 1998–99 | 2–0 | Hamilton Ricard, Gianluca Festa | 11,531 |
| 19 Sep 1998 | Premier League | H | Everton | Everton 1998–99 | 2–2 | Hamilton Ricard, Hamilton Ricard | 34,563 |
| 22 Sep 1998 | League Cup | A | Wycombe Wanderers | Wycombe Wanderers 1998–99 | 1–1 | Hamilton Ricard | 5,698 |
| 26 Sep 1998 | Premier League | A | Chelsea | Chelsea 1998–99 | 0–2 | 34,811 | |
| 3 Oct 1998 | Premier League | H | Sheffield Wednesday | Sheffield Wednesday 1998–99 | 4–0 | Mikkel Beck, Mikkel Beck, Hamilton Ricard, Paul Gascoigne | 34,163 |
| 17 Oct 1998 | Premier League | H | Blackburn Rovers | Blackburn Rovers 1998–99 | 2–1 | Hamilton Ricard, Curtis Fleming | 34,413 |
| 24 Oct 1998 | Premier League | A | Wimbledon | Wimbledon 1998–99 | 2–2 | Robbie Mustoe, Hamilton Ricard | 14,114 |
| 28 Oct 1998 | League Cup | H | Everton | Everton 1998–99 | 2–3 | Mark Summerbell, Hamilton Ricard | 20,748 |
| 1 Nov 1998 | Premier League | H | Nottingham Forest | Nottingham Forest 1998–99 | 1–1 | Brian Deane | 34,223 |
| 7 Nov 1998 | Premier League | A | Southampton | Southampton 1998–99 | 3–3 | Paul Gascoigne, Claus Lundekvam, Gianluca Festa | 15,202 |
| 14 Nov 1998 | Premier League | A | Charlton Athletic | Charlton Athletic 1998–99 | 1–1 | Phil Stamp | 20,043 |
| 21 Nov 1998 | Premier League | H | Coventry City | Coventry City 1998–99 | 2–0 | Dean Gordon, Hamilton Ricard | 34,293 |
| 29 Nov 1998 | Premier League | A | Arsenal | Arsenal 1998–99 | 1–1 | Brian Deane | 38,075 |
| 6 Dec 1998 | Premier League | H | Newcastle United | Newcastle United 1998–99 | 2–2 | Andy Townsend, Colin Cooper | 34,629 |
| 12 Dec 1998 | Premier League | H | West Ham United | West Ham United 1998–99 | 1–0 | Brian Deane | 34,623 |
| 19 Dec 1998 | Premier League | A | Manchester United | Manchester United 1998–99 | 3–2 | Hamilton Ricard, Dean Gordon, Brian Deane | 55,152 |
| 26 Dec 1998 | Premier League | H | Liverpool | Liverpool 1998–99 | 1–3 | Brian Deane | 34,626 |
| 28 Dec 1998 | Premier League | A | Derby County | Derby County 1998–99 | 1–2 | Mikkel Beck | 32,726 |
| 3 Jan 1999 | FA Cup | A | Manchester United | Manchester United 1998–99 | 1–3 | Andy Townsend | 52,232 |
| 9 Jan 1999 | Premier League | H | Aston Villa | Aston Villa 1998–99 | 0–0 | 34,643 | |
| 16 Jan 1999 | Premier League | A | Leeds United | Leeds United 1998–99 | 0–2 | 37,473 | |
| 30 Jan 1999 | Premier League | H | Leicester City | Leicester City 1998–99 | 0–0 | 34,631 | |
| 6 Feb 1999 | Premier League | A | Liverpool | Liverpool 1998–99 | 1–3 | Phil Stamp | 44,384 |
| 17 Feb 1999 | Premier League | A | Everton | Everton 1998–99 | 0–5 | 31,606 | |
| 20 Feb 1999 | Premier League | H | Tottenham Hotspur | Tottenham Hotspur 1998–99 | 0–0 | 34,687 | |
| 27 Feb 1999 | Premier League | A | Sheffield Wednesday | Sheffield Wednesday 1998–99 | 1–3 | Robbie Mustoe | 24,534 |
| 14 Mar 1999 | Premier League | H | Southampton | Southampton 1998–99 | 3–0 | Mikkel Beck, Hamilton Ricard, Steve Vickers | 33,387 |
| 20 Mar 1999 | Premier League | A | Nottingham Forest | Nottingham Forest 1998–99 | 2–1 | Hamilton Ricard, Brian Deane | 21,468 |
| 3 Apr 1999 | Premier League | A | Blackburn Rovers | Blackburn Rovers 1998–99 | 0–0 | 27,482 | |
| 5 Apr 1999 | Premier League | H | Wimbledon | Wimbledon 1998–99 | 3–1 | Hamilton Ricard, Hamilton Ricard, Gianluca Festa | 33,999 |
| 10 Apr 1999 | Premier League | H | Charlton Athletic | Charlton Athletic 1998–99 | 2–0 | Hamilton Ricard, Robbie Mustoe | 34,529 |
| 14 Apr 1999 | Premier League | H | Chelsea | Chelsea 1998–99 | 0–0 | 34,406 | |
| 17 Apr 1999 | Premier League | A | Coventry City | Coventry City 1998–99 | 2–1 | Vladimír Kinder, Dean Gordon | 19,231 |
| 24 Apr 1999 | Premier League | H | Arsenal | Arsenal 1998–99 | 1–6 | Alun Armstrong | 34,630 |
| 1 May 1999 | Premier League | A | Newcastle United | Newcastle United 1998–99 | 1–1 | Robbie Mustoe | 36,552 |
| 9 May 1999 | Premier League | H | Manchester United | Manchester United 1998–99 | 0–1 | 34,665 | |
| 16 May 1999 | Premier League | A | West Ham United | West Ham United 1998–99 | 0–4 | 25,902 |
54 of the goals in this season carry a named scorer.
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