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| Date | Match | Score |
|---|---|---|
| 23.01.2024 | Ipswich Town U21 - Middlesbrough U21 | 2 : 0 |
| 06.10.2023 | Middlesbrough U21 - Ipswich Town U21 | 2 : 0 |
| 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 |
| Date | Match | Score | Res |
|---|---|---|---|
| 11.09.2026 | Sunderland U21 - Ipswich Town U21 | 4 - 2 | L |
| 08.09.2026 | AFC Hornchurch - Ipswich Town U21 | 3 - 0 | L |
| 28.08.2026 | Ipswich Town U21 - Blackburn Rovers U21 | 4 - 1 | W |
| 24.08.2026 | Manchester United U21 - Ipswich Town U21 | 5 - 0 | L |
| 18.08.2026 | Braintree - Ipswich Town U21 | 1 - 1 | D |