| W | 2026-04-22 | Middlesbrough v Sheffield Weds | 1–0 | Championship |
| W | 2025-10-22 | Sheffield Weds v Middlesbrough | 0–1 | Championship |
| L | 2025-04-21 | Sheffield Weds v Middlesbrough | 2–1 | Championship |
| D | 2024-12-26 | Middlesbrough v Sheffield Weds | 3–3 | Championship |
| W | 2024-04-01 | Middlesbrough v Sheffield Weds | 2–0 | Championship |
| D | 2023-09-19 | Sheffield Weds v Middlesbrough | 1–1 | Championship |
| W | 2021-04-24 | Middlesbrough v Sheffield Weds | 3–1 | Championship |
| L | 2020-12-29 | Sheffield Weds v Middlesbrough | 2–1 | Championship |
| W | 2020-07-22 | Sheffield Weds v Middlesbrough | 1–2 | Championship |
| L | 2019-09-28 | Middlesbrough v Sheffield Weds | 1–4 | Championship |
| L | 2018-12-26 | Middlesbrough v Sheffield Weds | 0–1 | Championship |
| W | 2018-10-19 | Sheffield Weds v Middlesbrough | 1–2 | Championship |
| D | 2018-01-30 | Middlesbrough v Sheffield Weds | 0–0 | Championship |
| W | 2017-12-23 | Sheffield Weds v Middlesbrough | 1–2 | Championship |
| W | 2015-12-28 | Middlesbrough v Sheffield Weds | 1–0 | Championship |
| W | 2015-08-29 | Sheffield Weds v Middlesbrough | 1–3 | Championship |
| L | 2015-02-28 | Sheffield Weds v Middlesbrough | 2–0 | Championship |
| L | 2014-08-23 | Middlesbrough v Sheffield Weds | 2–3 | Championship |
| L | 2014-03-01 | Sheffield Weds v Middlesbrough | 1–0 | Championship |
| D | 2013-08-31 | Middlesbrough v Sheffield Weds | 1–1 | Championship |
| L | 2013-05-04 | Sheffield Weds v Middlesbrough | 2–0 | Championship |
| W | 2012-11-09 | Middlesbrough v Sheffield Weds | 3–1 | Championship |
| W | 2010-04-10 | Middlesbrough v Sheffield Weds | 1–0 | Championship |
| W | 2009-09-15 | Sheffield Weds v Middlesbrough | 1–3 | Championship |
| W | 2000-03-25 | Middlesbrough v Sheffield Weds | 1–0 | Premier League |