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| Date | Match | Score |
|---|
| Date | Match | Score | Res |
|---|---|---|---|
| 24.10.2026 | Chelsea U21 - Liverpool U21 | 2 - 2 | D |
| 16.10.2026 | Stoke City U21 - Chelsea U21 | 1 - 2 | W |
| 13.10.2026 | Reading - Chelsea U21 | 0 - 2 | W |
| 19.09.2026 | Chelsea U21 - Fulham U21 | 3 - 1 | W |
| 15.09.2026 | Wycombe - Chelsea U21 | 2 - 1 | L |
| Date | Match | Score | Res |
|---|---|---|---|
| 25.10.2026 | Middlesbrough U21 - Tottenham Hotspur U21 | 1 - 2 | L |
| 20.10.2026 | Boreham Wood - Middlesbrough U21 | 7 - 1 | L |
| 16.10.2026 | Everton U21 - Middlesbrough U21 | 2 - 1 | L |
| 30.09.2026 | Middlesbrough U21 - Juventus U21 | 1 - 0 | W |
| 23.09.2026 | Middlesbrough U21 - Genk U21 | 1 - 1 | D |