This page lists the head-to-head record of Bolton vs Middlesbrough including biggest victories and defeats between the two sides, and H2H stats in all competitions.
Overall H2H Record - Summary
| Total | Middlesbrough | Bolton | Draws |
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| Total Matches | 101 | 37 | 41 | 23 |
| At Riverside Stadium | 51 | 9 | 27 | 15 |
| At Macron Stadium | 50 | 28 | 14 | 8 |
| Carling Cup Matches | 1 | 1 | 0 | 0 |
| Premier League Matches | 84 | 25 | 37 | 22 |
| Championship Matches | 16 | 11 | 4 | 1 |
| Total Goals Scored | 319 | 161 | 158 | |
Last 50 Middlesbrough vs Bolton Matches
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| 2023 29 August | | Carling Cup | Bolton Wanderers | 1 - 3 | Middlesbrough |
| 2019 9 April | | Championship | Bolton Wanderers | 0 - 2 | Middlesbrough |
| 2018 19 September | | Championship | Middlesbrough | 2 - 0 | Bolton Wanderers |
| 2017 26 December | | Championship | Middlesbrough | 2 - 0 | Bolton Wanderers |
| 2017 9 September | | Championship | Bolton Wanderers | 0 - 3 | Middlesbrough |
| 2016 16 April | | Championship | Bolton Wanderers | 1 - 2 | Middlesbrough |
| 2015 15 August | | Championship | Middlesbrough | 3 - 0 | Bolton Wanderers |
| 2015 24 February | | Championship | Middlesbrough | 1 - 0 | Bolton Wanderers |
| 2014 19 August | | Championship | Bolton Wanderers | 1 - 2 | Middlesbrough |
| 2014 1 January | | Championship | Bolton Wanderers | 2 - 2 | Middlesbrough |
| 2013 30 November | | Championship | Middlesbrough | 1 - 0 | Bolton Wanderers |
| 2013 20 April | | Championship | Bolton Wanderers | 2 - 1 | Middlesbrough |
| 2012 27 October | | Championship | Middlesbrough | 2 - 1 | Bolton Wanderers |
| 2009 4 April | | Premier League | Bolton Wanderers | 4 - 1 | Middlesbrough |
| 2008 22 November | | Premier League | Middlesbrough | 1 - 3 | Bolton Wanderers |
| 2008 19 April | | Premier League | Middlesbrough | 0 - 1 | Bolton Wanderers |
| 2007 11 November | | Premier League | Bolton Wanderers | 0 - 0 | Middlesbrough |
| 2007 20 January | | Premier League | Middlesbrough | 5 - 1 | Bolton Wanderers |
| 2006 16 September | | Premier League | Bolton Wanderers | 0 - 0 | Middlesbrough |
| 2006 2 May | | Premier League | Bolton Wanderers | 1 - 1 | Middlesbrough |
| 2006 25 March | | Premier League | Middlesbrough | 4 - 3 | Bolton Wanderers |
| 2005 11 February | | Premier League | Bolton Wanderers | 0 - 0 | Middlesbrough |
| 2004 6 November | | Premier League | Middlesbrough | 1 - 1 | Bolton Wanderers |
| 2004 2 April | | Premier League | Middlesbrough | 2 - 0 | Bolton Wanderers |
| 2003 12 September | | Premier League | Bolton Wanderers | 2 - 0 | Middlesbrough |
| 2003 10 May | | Premier League | Bolton Wanderers | 2 - 1 | Middlesbrough |
| 2002 4 October | | Premier League | Middlesbrough | 2 - 0 | Bolton Wanderers |
| 2002 18 January | | Premier League | Middlesbrough | 1 - 1 | Bolton Wanderers |
| 2001 20 August | | Premier League | Bolton Wanderers | 1 - 0 | Middlesbrough |
| 1996 16 February | | Premier League | Middlesbrough | 1 - 4 | Bolton Wanderers |
| 1995 8 September | | Premier League | Bolton Wanderers | 1 - 1 | Middlesbrough |
| 1995 10 March | | Championship | Bolton Wanderers | 1 - 0 | Middlesbrough |
| 1994 26 August | | Championship | Middlesbrough | 1 - 0 | Bolton Wanderers |
| 1994 22 April | | Championship | Bolton Wanderers | 4 - 1 | Middlesbrough |
| 1993 20 November | | Championship | Middlesbrough | 0 - 1 | Bolton Wanderers |
| 1980 7 April | | Premier League | Bolton Wanderers | 2 - 2 | Middlesbrough |
| 1979 20 December | | Premier League | Middlesbrough | 3 - 1 | Bolton Wanderers |
| 1979 13 April | | Premier League | Bolton Wanderers | 0 - 0 | Middlesbrough |
| 1978 25 December | | Premier League | Middlesbrough | 1 - 1 | Bolton Wanderers |
| 1953 1 September | | Premier League | Middlesbrough | 3 - 2 | Bolton Wanderers |
| 1953 25 August | | Premier League | Bolton Wanderers | 3 - 2 | Middlesbrough |
| 1953 17 February | | Premier League | Bolton Wanderers | 5 - 3 | Middlesbrough |
| 1952 26 September | | Premier League | Middlesbrough | 1 - 2 | Bolton Wanderers |
| 1952 22 April | | Premier League | Middlesbrough | 2 - 0 | Bolton Wanderers |
| 1951 2 September | | Premier League | Bolton Wanderers | 3 - 1 | Middlesbrough |
| 1951 6 April | | Premier League | Middlesbrough | 1 - 1 | Bolton Wanderers |
| 1950 17 November | | Premier League | Bolton Wanderers | 0 - 2 | Middlesbrough |
| 1950 7 April | | Premier League | Middlesbrough | 2 - 0 | Bolton Wanderers |
| 1949 21 October | | Premier League | Bolton Wanderers | 1 - 2 | Middlesbrough |
| 1949 11 March | | Premier League | Bolton Wanderers | 4 - 1 | Middlesbrough |
Biggest Middlesbrough Victory vs Bolton
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| 1948 15 October | | Premier League | Middlesbrough | 5 - 0 | Bolton Wanderers |
Biggest Bolton Victory vs Middlesbrough
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| 1914 11 December | | Premier League | Bolton Wanderers | 4 - 0 | Middlesbrough |
Biggest Middlesbrough Defeat vs Bolton
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| 1914 11 December | | Premier League | Bolton Wanderers | 4 - 0 | Middlesbrough |
Biggest Bolton Defeat vs Middlesbrough
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| 1948 15 October | | Premier League | Middlesbrough | 5 - 0 | Bolton Wanderers |
Last 5 Middlesbrough Home Matches
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| 2026 4 January | | Championship | Middlesbrough | 4 - 0 | Southampton |
| 2025 29 December | | Championship | Middlesbrough | 0 - 1 | Hull City |
| 2025 26 December | | Championship | Middlesbrough | 0 - 0 | Blackburn Rovers |
| 2025 13 December | | Championship | Middlesbrough | 3 - 1 | Queens Park Rangers |
| 2025 29 November | | Championship | Middlesbrough | 2 - 1 | Derby County |
Last 5 Bolton Home Matches
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| 2026 4 January | | League One | Bolton Wanderers | 0 - 0 | Northampton Town |
| 2025 29 December | | League One | Bolton Wanderers | 0 - 1 | Mansfield Town |
| 2025 26 December | | League One | Bolton Wanderers | 2 - 1 | Rotherham United |
| 2025 13 December | | League One | Bolton Wanderers | 2 - 1 | Exeter City |
| 2025 2 December | | FL Trophy | Bolton Wanderers | 3 - 0 | Bradford City |
Last 5 Middlesbrough Away Matches
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| 2026 1 January | | Championship | Derby County | 1 - 0 | Middlesbrough |
| 2025 20 December | | Championship | Bristol City | 2 - 0 | Middlesbrough |
| 2025 9 December | | Championship | Charlton Athletic | 1 - 2 | Middlesbrough |
| 2025 5 December | | Championship | Hull City | 1 - 4 | Middlesbrough |
| 2025 22 November | | Championship | Oxford United | 1 - 1 | Middlesbrough |
Last 5 Bolton Away Matches
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| 2026 1 January | | League One | Doncaster Rovers | 1 - 1 | Bolton Wanderers |
| 2025 20 December | | League One | Wycombe Wanderers | 2 - 1 | Bolton Wanderers |
| 2025 9 December | | League One | Mansfield Town | 0 - 1 | Bolton Wanderers |
| 2025 6 December | | FA Cup | Swindon Town | 4 - 0 | Bolton Wanderers |
| 2025 29 November | | League One | Luton Town | 1 - 1 | Bolton Wanderers |