Middlesbrough have played York City 11 times in competitive football, winning 3, drawing 4 and losing 4, first meeting on 12 Feb 1938 and most recently on 18 Apr 1987. Every meeting is listed below.
| Date | Season | Competition | Venue | Opponent | Score | Scorers | Att |
|---|---|---|---|---|---|---|---|
| 12 Feb 1938 | 1937–38 | FA Cup | A | York City | 0–1 | ||
| 24 Aug 1966 | 1966–67 | League Cup | H | York City | 0–0 | ||
| 29 Aug 1966 | 1966–67 | League Cup | A | York City | 1–2 | ||
| 7 Jan 1967 | 1966–67 | FA Cup | H | York City | 1–1 | ||
| 11 Jan 1967 | 1966–67 | FA Cup | A | York City | 0–0 | ||
| 16 Jan 1967 | 1966–67 | FA Cup | H | York City | 4–1 | ||
| 24 Jan 1970 | 1969–70 | FA Cup | H | York City | 4–1 | ||
| 8 Sep 1971 | 1971–72 | League Cup | A | York City | 2–2 | ||
| 14 Sep 1971 | 1971–72 | League Cup | H | York City | 1–2 | ||
| 1 Jan 1987 | 1986–87 | Third Division | A | York City | 1–3 | 8,611 | |
| 18 Apr 1987 | 1986–87 | Third Division | H | York City | 3–1 | 10,546 |
All Middlesbrough head-to-head records · Middlesbrough season by season