| Club: | Middlesbrough |
| Season: | 1987-88 |
| Manager: | Bruce Rioch |
| League: | Football League Second Division |
| League Result: | 3rd (promoted) |
| League Topscorer: | Bernie Slaven |
| Season Topscorer: | Bernie Slaven |
| Highest Attendance: | Home: 27,645 (vs Leicester City) Away: 34,186 (vs Leeds United) |
| Lowest Attendance: | Home: 9,344 (vs Swindon Town) Away: 5,603 (vs Shrewsbury Town) |
| Cup1: | FA Cup |
| Cup1 Result: | 4th round |
| Cup2: | League Cup |
| Cup2 Result: | 2nd round |
| Cup3: | Simod Cup |
| Cup3 Result: | 1st round |
| Prevseason: | 1986–87 |
| Nextseason: | 1988–89 |
During the 1987–88 season, Middlesbrough participated in the Football League Second Division following their promotion the previous season. They were promoted to the First Division at the end of the season having finished third in the league and winning the play-offs.
During the 1987–88 season, Middlesbrough moved to a striped white top half on their home kit with the kits made by Skill and sponsored by Dickens.[1]
Appearance and goalscoring records for all the players who were in the Middlesbrough F.C. first team squad during the 1987–88 season.[2]
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| width=20% | Date | width=25% | Player | width=30% | Previous club | width=15% | Cost |
|---|---|---|---|---|---|---|---|
| August 1987 | Kevin Poole | Aston Villa | Free | ||||
| June 1987 | Dean Glover | Aston Villa | £60,000 | ||||
| December 1987 | Mark Burke | Aston Villa | £50,000 | ||||
| January 1988 |  Tony Cousins | Chelsea | Free | ||||
| March 1988 | Trevor Senior | Watford | £223,000 |
| width=20% | Date | width=25% | Player | width=30% | Buying club | width=15% | Cost |
|---|---|---|---|---|---|---|---|
| August 1987 | Lee Turnbull | Aston Villa | £59,000 | ||||
| July 1987 | Ronnie Coyle | Rochdale | Free | ||||
| December 1987 | Archie Stephens | Carlisle | Free |
Middlesbrough