| L | 2025-02-03 | Middlesbrough v Sunderland | 2–3 | Championship |
| L | 2024-09-21 | Sunderland v Middlesbrough | 1–0 | Championship |
| D | 2024-02-04 | Middlesbrough v Sunderland | 1–1 | Championship |
| W | 2023-10-07 | Sunderland v Middlesbrough | 0–4 | Championship |
| L | 2023-01-22 | Sunderland v Middlesbrough | 2–0 | Championship |
| W | 2022-09-05 | Middlesbrough v Sunderland | 1–0 | Championship |
| D | 2018-02-24 | Sunderland v Middlesbrough | 3–3 | Championship |
| W | 2017-11-05 | Middlesbrough v Sunderland | 1–0 | Championship |
| W | 2017-04-26 | Middlesbrough v Sunderland | 1–0 | Premier League |
| W | 2016-08-21 | Sunderland v Middlesbrough | 1–2 | Premier League |
| D | 2009-01-10 | Middlesbrough v Sunderland | 1–1 | Premier League |
| L | 2008-09-20 | Sunderland v Middlesbrough | 2–0 | Premier League |
| L | 2008-04-26 | Sunderland v Middlesbrough | 3–2 | Premier League |
| D | 2007-09-22 | Middlesbrough v Sunderland | 2–2 | Premier League |
| W | 2006-01-31 | Sunderland v Middlesbrough | 0–3 | Premier League |
| L | 2005-09-25 | Middlesbrough v Sunderland | 0–2 | Premier League |
| W | 2003-02-22 | Sunderland v Middlesbrough | 1–3 | Premier League |
| W | 2002-09-10 | Middlesbrough v Sunderland | 3–0 | Premier League |
| W | 2002-01-29 | Sunderland v Middlesbrough | 0–1 | Premier League |
| W | 2001-10-22 | Middlesbrough v Sunderland | 2–0 | Premier League |
| D | 2001-04-09 | Middlesbrough v Sunderland | 0–0 | Premier League |
| L | 2000-12-09 | Sunderland v Middlesbrough | 1–0 | Premier League |
| D | 2000-03-18 | Sunderland v Middlesbrough | 1–1 | Premier League |
| D | 1999-11-06 | Middlesbrough v Sunderland | 1–1 | Premier League |
| W | 1998-02-21 | Middlesbrough v Sunderland | 3–1 | Championship |