| Club: | Middlesbrough |
| Season: | 1989–90 |
| Manager: | Bruce Rioch/Colin Todd |
| Chairman: | Colin Henderson |
| Stadium: | Ayresome Park |
| League: | Second Division |
| League Result: | 21st |
| Cup1: | FA Cup |
| Cup1 Result: | Third round |
| Cup2: | League Cup |
| Cup2 Result: | Third round |
| Cup3: | Full Members' Cup |
| Cup3 Result: | Runners up |
| League Topscorer: | Slaven (21) |
| Season Topscorer: | Slaven (25) |
| Prevseason: | 1988–89 |
| Nextseason: | 1990–91 |
During the 1989–90 English football season, Middlesbrough F.C. competed in the Football League Second Division.
In the 1989–90 season, Boro finished 21st in the Second Division, only escaping relegation by two points with a dramatic end of season victory at home to local rivals Newcastle United.
Appearance and goalscoring records for all the players who were in the Middlesbrough F.C. first team squad during the 1989–90 season.[1]
|}
| Date | Player | Previous Club | Fee | |
|---|---|---|---|---|
| July 1989 | Trevor Putney | Norwich City | £342,000 | |
| March 1990 | Jimmy Phillips | Oxford United | £257,000 | |
| January 1990 | Ian Baird | Leeds United | £500,000 | |
| September 1989 |  Simon Coleman | Mansfield Town | Undisclosed |
See main article: 1989-90 FA Cup.
See main article: 1989–90 Football League Cup.
See main article: 1989–90 Full Members' Cup.