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| 23.01.2024 | LC | Chelsea FC | 6-1 | Middlesbrough | |
| 09.01.2024 | LC | Middlesbrough | 1-0 | Chelsea FC | |
| 19.03.2022 | Cup | Middlesbrough | 0-2 | Chelsea FC | |
| 08.05.2017 | PR | Chelsea FC | 3-0 | Middlesbrough | |
| 20.11.2016 | PR | Middlesbrough | 0-1 | Chelsea FC | |
| 27.02.2013 | Cup | Middlesbrough | 0-2 | Chelsea FC |
| GP | W | D | L | GF | GA | +/- | |
| home | 6 | 1 | 3 | 2 | 8 | 8 | 0 |
| away | 6 | 1 | 2 | 3 | 8 | 11 | -3 |
| total | 6 | 1 | 1 | 4 | 7 | 9 | -2 |
| Middlesbrough win | 17.64% | 6 |
| draw | 17.65% | 6 |
| Middlesbrough lose | 64.71% | 22 |
| GP | W | D | L | GF | GA | +/- | |
| home | 6 | 4 | 1 | 1 | 18 | 7 | 11 |
| away | 6 | 2 | 2 | 2 | 9 | 10 | -1 |
| total | 6 | 3 | 2 | 1 | 14 | 8 | 6 |
| Chelsea FC win | 64.70% | 22 |
| draw | 17.65% | 6 |
| Chelsea FC lose | 17.65% | 6 |
| 03.02.2025 | LCh | Middlesbrough | 2-3 | Sunderland |  |
| 25.01.2025 | LCh | Preston NE | 2-1 | Middlesbrough | |
| 21.01.2025 | LCh | Middlesbrough | 2-0 | West Bromwich |  |
| 18.01.2025 | LCh | Portsmouth | 2-1 | Middlesbrough | |
| 11.01.2025 | Cup | Middlesbrough | 0-1 | Blackburn Rovers | |
| 04.01.2025 | LCh | Middlesbrough | 1-1 | Cardiff City |  |
| 03.02.2025 | PR | Chelsea FC | 2-1 | West Ham | |
| 25.01.2025 | PR | Manchester City | 3-1 | Chelsea FC | |
| 20.01.2025 | PR | Chelsea FC | 3-1 | Wolverhampton | |
| 14.01.2025 | PR | Chelsea FC | 2-2 | Bournemouth | |
| 11.01.2025 | Cup | Chelsea FC | 5-0 | Morecambe FC | |
| 04.01.2025 | PR | Crystal Palace | 1-1 | Chelsea FC | |
| over 2.5 | 48.48% | 16 |
| under 2.5 | 51.52% | 17 |
| over 2.5 | 65.71% | 23 |
| under 2.5 | 34.29% | 12 |
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