Gary Hamilton
| Date of birth | 27 December 1965 |
| Place of birth | Glasgow |
| Nationality | Scottish |
| Position | Midfielder |
Club stats
| Season | Team | Competition | Apps | Subs | Goals | Y | R |
|---|---|---|---|---|---|---|---|
| 1982-83 | Middlesbrough | League Division Two | 8 | 1 |
2 |
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| 1983-84 | Middlesbrough | FA Cup | 3 | ||||
| 1983-84 | Middlesbrough | League Division Two | 26 | 5 |
3 |
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| 1984-85 | Middlesbrough | FA Cup | 2 | ||||
| 1984-85 | Middlesbrough | League Cup | 2 | ||||
| 1984-85 | Middlesbrough | League Division Two | 34 | 2 |
|||
| 1985-86 | Middlesbrough | FA Cup | 1 | ||||
| 1985-86 | Middlesbrough | League Cup | 1 | ||||
| 1985-86 | Middlesbrough | League Division Two | 33 | 4 |
|||
| 1986-87 | Middlesbrough | FA Cup | 2 | 1 |
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| 1986-87 | Middlesbrough | League Cup | 4 | 1 |
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| 1986-87 | Middlesbrough | League Division Three | 41 | 2 |
7 |
||
| 1987-88 | Middlesbrough | FA Cup | 5 | ||||
| 1987-88 | Middlesbrough | League Cup | 4 | ||||
| 1987-88 | Middlesbrough | League Division One and Two Play-Offs | 4 | 1 |
|||
| 1987-88 | Middlesbrough | League Division Two | 40 | 1 |
6 |
||
| 1988-89 | Middlesbrough | FA Cup | 1 | ||||
| 1988-89 | Middlesbrough | League Cup | 2 | ||||
| 1988-89 | Middlesbrough | League Division One | 35 | 1 |
3 |
Please note: Career stats are based on performances in the Premier and Football Leagues and (in most cases all) internationals.
Club matches
| Date | Match | Result | Competition | Round | |
|---|---|---|---|---|---|
| 26 Feb 1983 | Bolton Wanderers v Middlesbrough | L | 3-1 | League Division Two | |
| 19 Mar 1983 | Barnsley v Middlesbrough | L | 2-0 | League Division Two | |
| 05 Apr 1983 | Leicester City v Middlesbrough | L | 1-0 | League Division Two | |
| 16 Apr 1983 | Grimsby Town v Middlesbrough | W | 0-3 | League Division Two | |
| 23 Apr 1983 | Middlesbrough v Wolverhampton Wanderers | D | 0-0 | League Division Two | |
| 30 Apr 1983 | Blackburn Rovers v Middlesbrough | D | 1-1 | League Division Two | |
| 07 May 1983 | Middlesbrough v Cambridge United | L | 0-1 | League Division Two | |
| 10 May 1983 | Middlesbrough v Crystal Palace | W | 2-0 | League Division Two | |
| 14 May 1983 | Chelsea v Middlesbrough | D | 0-0 | League Division Two | |
| 06 Sep 1983 | Middlesbrough v Newcastle United | W | 3-2 | League Division Two | |
| 10 Sep 1983 | Barnsley v Middlesbrough | W | 0-2 | League Division Two | |
| 17 Sep 1983 | Middlesbrough v Grimsby Town | D | 1-1 | League Division Two | |
| 24 Sep 1983 | Chelsea v Middlesbrough | D | 0-0 | League Division Two | |
| 27 Sep 1983 | Fulham v Middlesbrough | L | 2-1 | League Division Two | |
| 08 Oct 1983 | Middlesbrough v Blackburn Rovers | L | 1-2 | League Division Two | |
| 19 Nov 1983 | Cambridge United v Middlesbrough | D | 0-0 | League Division Two | |
| 26 Nov 1983 | Middlesbrough v Swansea City | W | 1-0 | League Division Two | |
| 03 Dec 1983 | Charlton Athletic v Middlesbrough | L | 2-0 | League Division Two | |
| 10 Dec 1983 | Middlesbrough v Brighton and Hove Albion | D | 0-0 | League Division Two | |
| 17 Dec 1983 | Huddersfield Town v Middlesbrough | D | 2-2 | League Division Two | |
| 26 Dec 1983 | Middlesbrough v Carlisle United | L | 0-1 | League Division Two | |
| 31 Dec 1983 | Leeds United v Middlesbrough | L | 4-1 | League Division Two | |
| 02 Jan 1984 | Middlesbrough v Chelsea | W | 2-1 | League Division Two | |
| 07 Jan 1984 | Middlesbrough v Arsenal | W | 3-2 | FA Cup | 3rd round |
| 14 Jan 1984 | Middlesbrough v Portsmouth | D | 0-0 | League Division Two | |
| 21 Jan 1984 | Grimsby Town v Middlesbrough | D | 0-0 | League Division Two | |
| 31 Jan 1984 | Middlesbrough v AFC Bournemouth | W | 2-0 | FA Cup | 4th round |
| 04 Feb 1984 | Crystal Palace v Middlesbrough | L | 1-0 | League Division Two | |
| 11 Feb 1984 | Middlesbrough v Barnsley | W | 2-1 | League Division Two | |
| 18 Feb 1984 | Notts County v Middlesbrough | L | 1-0 | FA Cup | 5th round |
| 25 Feb 1984 | Middlesbrough v Manchester City | D | 0-0 | League Division Two | |
| 28 Feb 1984 | Shrewsbury Town v Middlesbrough | L | 1-0 | League Division Two | |
| 03 Mar 1984 | Cardiff City v Middlesbrough | L | 2-1 | League Division Two | |
| 17 Mar 1984 | Newcastle United v Middlesbrough | L | 3-1 | League Division Two | |
| 24 Mar 1984 | Middlesbrough v Fulham | L | 0-2 | League Division Two | |
| 31 Mar 1984 | Middlesbrough v Oldham Athletic | W | 3-2 | League Division Two | |
| 07 Apr 1984 | Blackburn Rovers v Middlesbrough | L | 1-0 | League Division Two | |
| 14 Apr 1984 | Middlesbrough v Cambridge United | D | 1-1 | League Division Two | |
| 20 Apr 1984 | Carlisle United v Middlesbrough | D | 1-1 | League Division Two | |
| 25 Apr 1984 | Middlesbrough v Sheffield Wednesday | W | 2-0 | League Division Two | |
| 05 May 1984 | Middlesbrough v Charlton Athletic | W | 1-0 | League Division Two | |
| 07 May 1984 | Brighton and Hove Albion v Middlesbrough | L | 3-0 | League Division Two | |
| 12 May 1984 | Middlesbrough v Huddersfield Town | D | 0-0 | League Division Two | |
| 25 Aug 1984 | Portsmouth v Middlesbrough | L | 1-0 | League Division Two | |
| 29 Aug 1984 | Bradford City v Middlesbrough | L | 2-0 | League Cup | 1st round 1st leg |
| 01 Sep 1984 | Middlesbrough v Grimsby Town | L | 1-5 | League Division Two | |
| 04 Sep 1984 | Middlesbrough v Bradford City | D |
2-2 Agg: 2-4 |
League Cup | 1st round 2nd leg |
| 08 Sep 1984 | Notts County v Middlesbrough | L | 3-2 | League Division Two | |
| 29 Sep 1984 | Middlesbrough v Cardiff City | W | 3-2 | League Division Two | |
| 06 Oct 1984 | Middlesbrough v Charlton Athletic | W | 1-0 | League Division Two | |
| 13 Oct 1984 | Sheffield United v Middlesbrough | W | 0-3 | League Division Two | |
| 20 Oct 1984 | Middlesbrough v Manchester City | W | 2-1 | League Division Two | |
| 27 Oct 1984 | Leeds United v Middlesbrough | L | 2-0 | League Division Two | |
| 03 Nov 1984 | Huddersfield Town v Middlesbrough | L | 3-1 | League Division Two | |
| 10 Nov 1984 | Middlesbrough v Barnsley | D | 0-0 | League Division Two | |
| 17 Nov 1984 | Middlesbrough v Blackburn Rovers | L | 1-2 | League Division Two | |
| 24 Nov 1984 | Brighton and Hove Albion v Middlesbrough | W | 1-2 | League Division Two | |
| 01 Dec 1984 | Middlesbrough v Crystal Palace | D | 1-1 | League Division Two | |
| 08 Dec 1984 | Birmingham City v Middlesbrough | L | 3-2 | League Division Two | |
| 14 Dec 1984 | Middlesbrough v Shrewsbury Town | D | 1-1 | League Division Two | |
| 22 Dec 1984 | Grimsby Town v Middlesbrough | L | 3-1 | League Division Two | |
| 26 Dec 1984 | Carlisle United v Middlesbrough | W | 0-3 | League Division Two | |
| 01 Jan 1985 | Middlesbrough v Oxford United | L | 0-1 | League Division Two | |
| 05 Jan 1985 | Middlesbrough v Darlington | D | 0-0 | FA Cup | 3rd round |
| 08 Jan 1985 | Darlington v Middlesbrough | L | 2-1 | FA Cup | 3rd round replay |
| 12 Jan 1985 | Wolverhampton Wanderers v Middlesbrough | D | 0-0 | League Division Two | |
| 19 Jan 1985 | Middlesbrough v Portsmouth | D | 0-0 | League Division Two | |
| 02 Feb 1985 | Cardiff City v Middlesbrough | L | 2-1 | League Division Two | |
| 23 Feb 1985 | Middlesbrough v Huddersfield Town | D | 2-2 | League Division Two | |
| 26 Feb 1985 | Barnsley v Middlesbrough | L | 1-0 | League Division Two | |
| 02 Mar 1985 | Middlesbrough v Leeds United | D | 0-0 | League Division Two | |
| 09 Mar 1985 | Manchester City v Middlesbrough | L | 1-0 | League Division Two | |
| 16 Mar 1985 | Middlesbrough v Sheffield United | W | 1-0 | League Division Two | |
| 22 Mar 1985 | Charlton Athletic v Middlesbrough | L | 1-0 | League Division Two | |
| 30 Mar 1985 | Wimbledon v Middlesbrough | D | 1-1 | League Division Two | |
| 06 Apr 1985 | Middlesbrough v Carlisle United | L | 1-2 | League Division Two | |
| 08 Apr 1985 | Oxford United v Middlesbrough | L | 1-0 | League Division Two | |
| 13 Apr 1985 | Middlesbrough v Fulham | W | 2-0 | League Division Two | |
| 20 Apr 1985 | Blackburn Rovers v Middlesbrough | L | 3-0 | League Division Two | |
| 27 Apr 1985 | Middlesbrough v Brighton and Hove Albion | W | 2-1 | League Division Two | |
| 04 May 1985 | Crystal Palace v Middlesbrough | L | 1-0 | League Division Two | |
| 06 May 1985 | Middlesbrough v Birmingham City | D | 0-0 | League Division Two | |
| 11 May 1985 | Shrewsbury Town v Middlesbrough | W | 0-2 | League Division Two | |
| 24 Aug 1985 | Middlesbrough v Fulham | W | 1-0 | League Division Two | |
| 27 Aug 1985 | Charlton Athletic v Middlesbrough | L | 2-0 | League Division Two | |
| 31 Aug 1985 | Middlesbrough v Brighton and Hove Albion | L | 0-1 | League Division Two | |
| 03 Sep 1985 | Middlesbrough v Mansfield Town | D |
4-4 Agg: 4-6 |
League Cup | 1st round 2nd leg |
| 21 Sep 1985 | Sheffield United v Middlesbrough | W | 0-1 | League Division Two | |
| 28 Sep 1985 | Middlesbrough v Barnsley | D | 0-0 | League Division Two | |
| 05 Oct 1985 | Middlesbrough v Crystal Palace | L | 0-2 | League Division Two | |
| 12 Oct 1985 | Leeds United v Middlesbrough | L | 1-0 | League Division Two | |
| 19 Oct 1985 | Middlesbrough v Bradford City | D | 1-1 | League Division Two | |
| 22 Oct 1985 | Sunderland v Middlesbrough | L | 1-0 | League Division Two | |
| 26 Oct 1985 | Grimsby Town v Middlesbrough | L | 3-2 | League Division Two | |
| 02 Nov 1985 | Middlesbrough v Blackburn Rovers | D | 0-0 | League Division Two | |
| 16 Nov 1985 | Middlesbrough v Oldham Athletic | W | 3-2 | League Division Two | |
| 23 Nov 1985 | Millwall v Middlesbrough | L | 3-0 | League Division Two | |
| 30 Nov 1985 | Middlesbrough v Shrewsbury Town | W | 3-1 | League Division Two | |
| 07 Dec 1985 | Stoke City v Middlesbrough | L | 3-2 | League Division Two | |
| 14 Dec 1985 | Middlesbrough v Wimbledon | W | 1-0 | League Division Two | |
| 21 Dec 1985 | Fulham v Middlesbrough | W | 0-3 | League Division Two | |
| 26 Dec 1985 | Carlisle United v Middlesbrough | L | 1-0 | League Division Two | |
| 28 Dec 1985 | Middlesbrough v Sunderland | W | 2-0 | League Division Two | |
| 01 Jan 1986 | Middlesbrough v Huddersfield Town | L | 0-1 | League Division Two | |
| 11 Jan 1986 | Norwich City v Middlesbrough | L | 2-0 | League Division Two | |
| 13 Jan 1986 | Middlesbrough v Southampton | L | 1-3 | FA Cup | 3rd round |
| 18 Jan 1986 | Brighton and Hove Albion v Middlesbrough | D | 3-3 | League Division Two | |
| 25 Jan 1986 | Portsmouth v Middlesbrough | L | 1-0 | League Division Two | |
| 01 Feb 1986 | Middlesbrough v Charlton Athletic | L | 1-3 | League Division Two | |
| 25 Mar 1986 | Barnsley v Middlesbrough | D | 0-0 | League Division Two | |
| 29 Mar 1986 | Huddersfield Town v Middlesbrough | W | 0-3 | League Division Two | |
| 31 Mar 1986 | Middlesbrough v Carlisle United | L | 1-3 | League Division Two | |
| 05 Apr 1986 | Blackburn Rovers v Middlesbrough | W | 0-1 | League Division Two | |
| 12 Apr 1986 | Middlesbrough v Portsmouth | W | 1-0 | League Division Two | |
| 19 Apr 1986 | Oldham Athletic v Middlesbrough | L | 1-0 | League Division Two | |
| 23 Apr 1986 | Bradford City v Middlesbrough | L | 2-1 | League Division Two | |
| 26 Apr 1986 | Middlesbrough v Millwall | W | 3-0 | League Division Two | |
| 03 May 1986 | Shrewsbury Town v Middlesbrough | L | 2-1 | League Division Two | |
| 23 Aug 1986 | Middlesbrough v Port Vale | D | 2-2 | League Division Three | |
| 26 Aug 1986 | Hartlepool United v Middlesbrough | D | 1-1 | League Cup | 1st round 1st leg |
| 30 Aug 1986 | Wigan Athletic v Middlesbrough | W | 0-2 | League Division Three | |
| 02 Sep 1986 | Middlesbrough v Hartlepool United | W |
2-0 Agg: 3-1 |
League Cup | 1st round 2nd leg |
| 06 Sep 1986 | Middlesbrough v Bury | W | 3-1 | League Division Three | |
| 13 Sep 1986 | Gillingham v Middlesbrough | D | 0-0 | League Division Three | |
| 17 Sep 1986 | Bristol Rovers v Middlesbrough | W | 1-2 | League Division Three | |
| 20 Sep 1986 | Middlesbrough v Chesterfield | W | 2-0 | League Division Three | |
| 23 Sep 1986 | Middlesbrough v Birmingham City | D | 2-2 | League Cup | 2nd round 1st leg |
| 27 Sep 1986 | Fulham v Middlesbrough | D | 2-2 | League Division Three | |
| 30 Sep 1986 | Middlesbrough v Swindon Town | W | 1-0 | League Division Three | |
| 04 Oct 1986 | Rotherham United v Middlesbrough | W | 1-4 | League Division Three | |
| 07 Oct 1986 | Birmingham City v Middlesbrough | L |
3-2 Agg: 5-4 |
League Cup | 2nd round 2nd leg |
| 11 Oct 1986 | Middlesbrough v Blackpool | L | 1-3 | League Division Three | |
| 18 Oct 1986 | Middlesbrough v Walsall | W | 3-1 | League Division Three | |
| 21 Oct 1986 | Notts County v Middlesbrough | L | 1-0 | League Division Three | |
| 25 Oct 1986 | Bristol City v Middlesbrough | D | 2-2 | League Division Three | |
| 01 Nov 1986 | Middlesbrough v AFC Bournemouth | W | 4-0 | League Division Three | |
| 04 Nov 1986 | Middlesbrough v Bolton Wanderers | D | 0-0 | League Division Three | |
| 22 Nov 1986 | Newport County v Middlesbrough | W | 0-1 | League Division Three | |
| 29 Nov 1986 | Middlesbrough v Chester City | L | 1-2 | League Division Three | |
| 07 Dec 1986 | Notts County v Middlesbrough | W | 0-1 | FA Cup | 2nd round |
| 13 Dec 1986 | Middlesbrough v Doncaster Rovers | W | 1-0 | League Division Three | |
| 21 Dec 1986 | Brentford v Middlesbrough | W | 0-1 | League Division Three | |
| 26 Dec 1986 | Middlesbrough v Carlisle United | W | 1-0 | League Division Three | |
| 27 Dec 1986 | Mansfield Town v Middlesbrough | D | 1-1 | League Division Three | |
| 01 Jan 1987 | York City v Middlesbrough | L | 3-1 | League Division Three | |
| 03 Jan 1987 | Middlesbrough v Newport County | W | 2-0 | League Division Three | |
| 10 Jan 1987 | Middlesbrough v Preston North End | L | 0-1 | FA Cup | 3rd round |
| 14 Feb 1987 | Chesterfield v Middlesbrough | L | 2-1 | League Division Three | |
| 17 Feb 1987 | Port Vale v Middlesbrough | D | 0-0 | League Division Three | |
| 21 Feb 1987 | Middlesbrough v Fulham | W | 3-0 | League Division Three | |
| 28 Feb 1987 | Swindon Town v Middlesbrough | L | 1-0 | League Division Three | |
| 03 Mar 1987 | AFC Bournemouth v Middlesbrough | L | 3-1 | League Division Three | |
| 07 Mar 1987 | Middlesbrough v Bristol City | W | 1-0 | League Division Three | |
| 14 Mar 1987 | Walsall v Middlesbrough | L | 1-0 | League Division Three | |
| 17 Mar 1987 | Middlesbrough v Notts County | W | 2-0 | League Division Three | |
| 21 Mar 1987 | Blackpool v Middlesbrough | W | 0-1 | League Division Three | |
| 28 Mar 1987 | Middlesbrough v Rotherham United | D | 0-0 | League Division Three | |
| 05 Apr 1987 | Middlesbrough v Darlington | D | 1-1 | League Division Three | |
| 11 Apr 1987 | Bolton Wanderers v Middlesbrough | W | 0-1 | League Division Three | |
| 18 Apr 1987 | Middlesbrough v York City | W | 3-1 | League Division Three | |
| 20 Apr 1987 | Carlisle United v Middlesbrough | W | 0-1 | League Division Three | |
| 25 Apr 1987 | Middlesbrough v Brentford | W | 2-0 | League Division Three | |
| 28 Apr 1987 | Middlesbrough v Gillingham | W | 3-0 | League Division Three | |
| 02 May 1987 | Chester City v Middlesbrough | W | 1-2 | League Division Three | |
| 04 May 1987 | Middlesbrough v Mansfield Town | W | 1-0 | League Division Three | |
| 06 May 1987 | Middlesbrough v Wigan Athletic | D | 0-0 | League Division Three | |
| 09 May 1987 | Doncaster Rovers v Middlesbrough | W | 0-2 | League Division Three | |
| 15 Aug 1987 | Middlesbrough v Millwall | D | 1-1 | League Division Two | |
| 18 Aug 1987 | Sunderland v Middlesbrough | L | 1-0 | League Cup | 1st round 1st leg |
| 22 Aug 1987 | Stoke City v Middlesbrough | L | 1-0 | League Division Two | |
| 25 Aug 1987 | Middlesbrough v Sunderland | W |
2-0 Agg: 2-1 |
League Cup | 1st round 2nd leg |
| 29 Aug 1987 | Middlesbrough v Oldham Athletic | W | 1-0 | League Division Two | |
| 01 Sep 1987 | Crystal Palace v Middlesbrough | L | 3-1 | League Division Two | |
| 05 Sep 1987 | Middlesbrough v Swindon Town | L | 2-3 | League Division Two | |
| 08 Sep 1987 | Aston Villa v Middlesbrough | W | 0-1 | League Division Two | |
| 15 Sep 1987 | Middlesbrough v AFC Bournemouth | W | 3-0 | League Division Two | |
| 19 Sep 1987 | Middlesbrough v Leeds United | W | 2-0 | League Division Two | |
| 23 Sep 1987 | Middlesbrough v Aston Villa | L | 0-1 | League Cup | 2nd round 1st leg |
| 26 Sep 1987 | Blackburn Rovers v Middlesbrough | W | 0-2 | League Division Two | |
| 29 Sep 1987 | Middlesbrough v Reading | D | 0-0 | League Division Two | |
| 03 Oct 1987 | Bradford City v Middlesbrough | L | 2-0 | League Division Two | |
| 07 Oct 1987 | Aston Villa v Middlesbrough | L |
1-0 Agg: 2-0 |
League Cup | 2nd round 2nd leg |
| 10 Oct 1987 | Huddersfield Town v Middlesbrough | W | 1-4 | League Division Two | |
| 17 Oct 1987 | Middlesbrough v West Bromwich Albion | W | 2-1 | League Division Two | |
| 20 Oct 1987 | Middlesbrough v Ipswich Town | W | 3-1 | League Division Two | |
| 24 Oct 1987 | Birmingham City v Middlesbrough | D | 0-0 | League Division Two | |
| 31 Oct 1987 | Middlesbrough v Shrewsbury Town | W | 4-0 | League Division Two | |
| 04 Nov 1987 | Manchester City v Middlesbrough | D | 1-1 | League Division Two | |
| 07 Nov 1987 | Sheffield United v Middlesbrough | W | 0-2 | League Division Two | |
| 14 Nov 1987 | Middlesbrough v Hull City | W | 1-0 | League Division Two | |
| 21 Nov 1987 | Plymouth Argyle v Middlesbrough | W | 0-1 | League Division Two | |
| 28 Nov 1987 | Middlesbrough v Barnsley | W | 2-0 | League Division Two | |
| 05 Dec 1987 | Leicester City v Middlesbrough | D | 0-0 | League Division Two | |
| 12 Dec 1987 | Middlesbrough v Stoke City | W | 2-0 | League Division Two | |
| 19 Dec 1987 | AFC Bournemouth v Middlesbrough | D | 0-0 | League Division Two | |
| 26 Dec 1987 | Middlesbrough v Blackburn Rovers | D | 1-1 | League Division Two | |
| 28 Dec 1987 | Leeds United v Middlesbrough | L | 2-0 | League Division Two | |
| 01 Jan 1988 | Oldham Athletic v Middlesbrough | L | 3-1 | League Division Two | |
| 09 Jan 1988 | Sutton United v Middlesbrough | D | 1-1 | FA Cup | 3rd round |
| 12 Jan 1988 | Middlesbrough v Sutton United | W | 1-0 | FA Cup | 3rd round replay |
| 16 Jan 1988 | Millwall v Middlesbrough | L | 2-1 | League Division Two | |
| 23 Jan 1988 | Middlesbrough v Crystal Palace | W | 2-1 | League Division Two | |
| 30 Jan 1988 | Everton v Middlesbrough | D | 1-1 | FA Cup | 4th round |
| 03 Feb 1988 | Middlesbrough v Everton | D | 2-2 | FA Cup | 4th round replay |
| 06 Feb 1988 | Swindon Town v Middlesbrough | D | 1-1 | League Division Two | |
| 09 Feb 1988 | Everton v Middlesbrough | L | 2-1 | FA Cup | 4th round 2nd replay |
| 14 Feb 1988 | Middlesbrough v Aston Villa | W | 2-1 | League Division Two | |
| 20 Feb 1988 | Reading v Middlesbrough | D | 0-0 | League Division Two | |
| 27 Feb 1988 | Middlesbrough v Bradford City | L | 1-2 | League Division Two | |
| 05 Mar 1988 | West Bromwich Albion v Middlesbrough | D | 0-0 | League Division Two | |
| 19 Mar 1988 | Shrewsbury Town v Middlesbrough | W | 0-1 | League Division Two | |
| 26 Mar 1988 | Middlesbrough v Birmingham City | D | 1-1 | League Division Two | |
| 09 Apr 1988 | Middlesbrough v Manchester City | W | 2-1 | League Division Two | |
| 23 Apr 1988 | Ipswich Town v Middlesbrough | L | 4-0 | League Division Two | |
| 30 Apr 1988 | Middlesbrough v Plymouth Argyle | W | 3-1 | League Division Two | |
| 02 May 1988 | Barnsley v Middlesbrough | W | 0-3 | League Division Two | |
| 07 May 1988 | Middlesbrough v Leicester City | L | 1-2 | League Division Two | |
| 15 May 1988 | Bradford City v Middlesbrough | L | 2-1 | League Division One and Two Play-Offs | Semi-final 1st leg |
| 18 May 1988 | Middlesbrough v Bradford City | W |
2-0 Agg: 3-2 |
League Division One and Two Play-Offs | Semi-final 2nd leg |
| 25 May 1988 | Middlesbrough v Chelsea | W | 2-0 | League Division One and Two Play-Offs | Final 1st leg |
| 28 May 1988 | Chelsea v Middlesbrough | L |
1-0 Agg: 1-2 |
League Division One and Two Play-Offs | Final 2nd leg |
| 27 Aug 1988 | Derby County v Middlesbrough | L | 1-0 | League Division One | |
| 03 Sep 1988 | Middlesbrough v Norwich City | L | 2-3 | League Division One | |
| 10 Sep 1988 | Manchester United v Middlesbrough | L | 1-0 | League Division One | |
| 17 Sep 1988 | Middlesbrough v Wimbledon | W | 1-0 | League Division One | |
| 24 Sep 1988 | Tottenham Hotspur v Middlesbrough | L | 3-2 | League Division One | |
| 28 Sep 1988 | Middlesbrough v Tranmere Rovers | D | 0-0 | League Cup | 2nd round 1st leg |
| 01 Oct 1988 | Coventry City v Middlesbrough | W | 3-4 | League Division One | |
| 08 Oct 1988 | Middlesbrough v West Ham United | W | 1-0 | League Division One | |
| 11 Oct 1988 | Tranmere Rovers v Middlesbrough | L |
1-0 Agg: 1-0 |
League Cup | 2nd round 2nd leg |
| 22 Oct 1988 | Middlesbrough v Luton Town | W | 2-1 | League Division One | |
| 26 Oct 1988 | Newcastle United v Middlesbrough | L | 3-0 | League Division One | |
| 29 Oct 1988 | Middlesbrough v Millwall | W | 4-2 | League Division One | |
| 05 Nov 1988 | Liverpool v Middlesbrough | L | 3-0 | League Division One | |
| 12 Nov 1988 | Middlesbrough v Queens Park Rangers | W | 1-0 | League Division One | |
| 19 Nov 1988 | Arsenal v Middlesbrough | L | 3-0 | League Division One | |
| 26 Nov 1988 | Middlesbrough v Sheffield Wednesday | L | 0-1 | League Division One | |
| 03 Dec 1988 | Nottingham Forest v Middlesbrough | D | 2-2 | League Division One | |
| 10 Dec 1988 | Middlesbrough v Aston Villa | D | 3-3 | League Division One | |
| 17 Dec 1988 | Middlesbrough v Charlton Athletic | D | 0-0 | League Division One | |
| 26 Dec 1988 | Everton v Middlesbrough | L | 2-1 | League Division One | |
| 31 Dec 1988 | Norwich City v Middlesbrough | D | 0-0 | League Division One | |
| 02 Jan 1989 | Middlesbrough v Manchester United | W | 1-0 | League Division One | |
| 07 Jan 1989 | Middlesbrough v Grimsby Town | L | 1-2 | FA Cup | 3rd round |
| 14 Jan 1989 | Southampton v Middlesbrough | W | 1-3 | League Division One | |
| 21 Jan 1989 | Middlesbrough v Tottenham Hotspur | D | 2-2 | League Division One | |
| 04 Feb 1989 | Middlesbrough v Coventry City | D | 1-1 | League Division One | |
| 18 Feb 1989 | Luton Town v Middlesbrough | L | 1-0 | League Division One | |
| 21 Feb 1989 | Millwall v Middlesbrough | L | 2-0 | League Division One | |
| 26 Feb 1989 | Middlesbrough v Newcastle United | D | 1-1 | League Division One | |
| 11 Mar 1989 | Middlesbrough v Liverpool | L | 0-4 | League Division One | |
| 18 Mar 1989 | Middlesbrough v Derby County | L | 0-1 | League Division One | |
| 01 Apr 1989 | Charlton Athletic v Middlesbrough | L | 2-0 | League Division One | |
| 08 Apr 1989 | Middlesbrough v Southampton | D | 3-3 | League Division One | |
| 11 Apr 1989 | West Ham United v Middlesbrough | W | 1-2 | League Division One | |
| 15 Apr 1989 | Queens Park Rangers v Middlesbrough | D | 0-0 | League Division One | |
| 22 Apr 1989 | Middlesbrough v Nottingham Forest | L | 3-4 | League Division One | |
| 29 Apr 1989 | Aston Villa v Middlesbrough | D | 1-1 | League Division One | |
| 06 May 1989 | Middlesbrough v Arsenal | L | 0-1 | League Division One | |
| 13 May 1989 | Sheffield Wednesday v Middlesbrough | L | 1-0 | League Division One | |
Please note: Match history is complete for the Premier and Football Leagues and (in most cases all) internationals.