| D | 2026-02-24 | Middlesbrough v Leicester | 1–1 | Championship |
| D | 2025-11-04 | Leicester v Middlesbrough | 1–1 | Championship |
| L | 2024-02-17 | Leicester v Middlesbrough | 1–2 | Championship |
| L | 2023-11-11 | Middlesbrough v Leicester | 1–0 | Championship |
| D | 2017-01-02 | Middlesbrough v Leicester | 0–0 | Premier League |
| D | 2016-11-26 | Leicester v Middlesbrough | 2–2 | Premier League |
| W | 2014-01-25 | Leicester v Middlesbrough | 2–0 | Championship |
| W | 2013-08-03 | Middlesbrough v Leicester | 1–2 | Championship |
| W | 2013-01-18 | Leicester v Middlesbrough | 1–0 | Championship |
| W | 2012-09-29 | Middlesbrough v Leicester | 1–2 | Championship |
| D | 2012-02-01 | Leicester v Middlesbrough | 2–2 | Championship |
| D | 2011-09-28 | Middlesbrough v Leicester | 0–0 | Championship |
| D | 2011-04-02 | Middlesbrough v Leicester | 3–3 | Championship |
| D | 2010-08-14 | Leicester v Middlesbrough | 0–0 | Championship |
| W | 2010-05-02 | Leicester v Middlesbrough | 2–0 | Championship |
| W | 2009-09-29 | Middlesbrough v Leicester | 0–1 | Championship |
| D | 2004-01-17 | Middlesbrough v Leicester | 3–3 | Premier League |
| D | 2003-08-26 | Leicester v Middlesbrough | 0–0 | Premier League |
| L | 2002-03-02 | Middlesbrough v Leicester | 1–0 | Premier League |
| L | 2001-09-17 | Leicester v Middlesbrough | 1–2 | Premier League |
| L | 2001-04-21 | Leicester v Middlesbrough | 0–3 | Premier League |
| W | 2000-11-18 | Middlesbrough v Leicester | 0–3 | Premier League |
| W | 2000-02-05 | Leicester v Middlesbrough | 2–1 | Premier League |
| W | 1999-08-24 | Middlesbrough v Leicester | 0–3 | Premier League |
| D | 1999-01-30 | Middlesbrough v Leicester | 0–0 | Premier League |