[17] Charlton 1-2 Middlesbrough [2] 2025-10-01 05:45
Stadium: The Valley Round: 20
Referee: Oliver Langford Home Manager: Nathan Jones Away Manager: Kim Hellberg
Head to Head
| England Championship | 2020/03/07 15:00 | Charlton v Middlesbrough | L | 0-1 |
| England Championship | 2019/12/07 15:00 | Middlesbrough v Charlton | L | 1-0 |
| England Championship | 2016/03/13 15:30 | Charlton v Middlesbrough | W | 2-0 |
| England Championship | 2015/10/31 15:00 | Middlesbrough v Charlton | L | 3-0 |
| England Championship | 2015/02/07 15:00 | Middlesbrough v Charlton | L | 3-1 |
| England Championship | 2014/09/27 14:00 | Charlton v Middlesbrough | D | 0-0 |
Home History
| England Championship | 2025/09/30 19:00 | Derby v Charlton | D | 1-1 |
| England Championship | 2025/09/27 14:00 | Charlton v Blackburn | W | 3-0 |
| England Championship | 2025/09/20 14:00 | Sheff Utd v Charlton | W | 0-1 |
| England Championship | 2025/09/13 11:30 | Charlton v Millwall | D | 1-1 |
| England Championship | 2025/08/30 11:30 | QPR v Charlton | L | 3-1 |
| England EFL Cup | 2025/08/26 18:30 | Cambridge Utd v Charlton | L | 3-1 |
| England Championship | 2025/08/23 11:30 | Charlton v Leicester | L | 0-1 |
| England Championship | 2025/08/16 14:00 | Bristol City v Charlton | D | 0-0 |
Away History
| England Championship | 2025/09/30 18:45 | Middlesbrough v Stoke | D | 0-0 |
| England Championship | 2025/09/27 14:00 | Southampton v Middlesbrough | D | 1-1 |
| England Championship | 2025/09/19 19:00 | Middlesbrough v West Brom | W | 2-1 |
| England Championship | 2025/09/13 11:30 | Preston v Middlesbrough | D | 2-2 |
| England Championship | 2025/08/30 11:30 | Middlesbrough v Sheff Utd | W | 1-0 |
| England Championship | 2025/08/23 14:00 | Norwich v Middlesbrough | W | 1-2 |
| England Championship | 2025/08/16 14:00 | Millwall v Middlesbrough | W | 0-3 |
| England EFL Cup | 2025/08/12 18:30 | Middlesbrough v Doncaster | L | 0-4 |