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| Date | Match | Score |
|---|
| Date | Match | Score | Res |
|---|---|---|---|
| 31.08.2026 | Chelsea U21 - West Ham United U21 | 5 - 4 | W |
| 25.08.2026 | Bristol Rovers - Chelsea U21 | 2 - 2 | D |
| 21.08.2026 | AFC Bournemouth U21 - Chelsea U21 | 2 - 1 | L |
| 04.08.2026 | Boreham Wood - Chelsea U21 | - | |
| 21.07.2026 | Chelsea U21 - Cardiff City U21 | 0 - 0 | D |
| Date | Match | Score | Res |
|---|---|---|---|
| 09.09.2026 | Tamworth - Middlesbrough U21 | 1 - 3 | W |
| 31.08.2026 | AFC Bournemouth U21 - Middlesbrough U21 | 3 - 1 | L |
| 23.08.2026 | Middlesbrough U21 - Norwich City U21 | 0 - 1 | L |
| 18.08.2026 | Solihull Moors - Middlesbrough U21 | 1 - 3 | W |
| 11.08.2026 | Hartlepool - Middlesbrough U21 | 0 - 10 | W |