Wycombe Wanderers have played Middlesbrough 6 times in competitive football, winning 1, drawing 2 and losing 3, first meeting on 4 Jan 1975 and most recently on 8 May 2021. Every meeting is listed below.
| Date | Season | Competition | Venue | Opponent | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 4 Jan 1975 | 1974–75 | FA Cup | H | Middlesbrough | 0–0 | 12,000 | |
| 7 Jan 1975 | 1974–75 | FA Cup | A | Middlesbrough | 0–1 | 30,128 | |
| 16 Sep 1998 | 1998–99 | League Cup | A | Middlesbrough | 0–2 | ||
| 22 Sep 1998 | 1998–99 | League Cup | H | Middlesbrough | 1–1 | ||
| 2 Jan 2021 | 2020–21 | Championship | H | Middlesbrough | 1–3 | Uche Ikpeazu 3 | |
| 8 May 2021 | 2020–21 | Championship | A | Middlesbrough | 3–0 | Fred Onyedinma 14, Garath McCleary 33, Jason McCarthy 56 |
See also: the Middlesbrough archive and Middlesbrough v Wycombe Wanderers.
All Wycombe Wanderers head-to-head records · Wycombe Wanderers season by season