Stadium: Stamford Bridge Round: 23
Referee: Tim Robinson Home Manager: Mauricio Pochettino Away Manager: Gary O'Neil
| England Premier League | 2023/12/24 13:00 | Wolverhampton v Chelsea | L | 2-1 |
| England Premier League | 2023/04/08 14:00 | Wolverhampton v Chelsea | L | 1-0 |
| England Premier League | 2022/10/08 14:00 | Chelsea v Wolverhampton | W | 3-0 |
| England Premier League | 2022/05/07 14:00 | Chelsea v Wolverhampton | D | 2-2 |
| England Premier League | 2021/12/19 14:00 | Wolverhampton v Chelsea | D | 0-0 |
| England Premier League | 2021/01/27 18:00 | Chelsea v Wolverhampton | D | 0-0 |
| England Premier League | 2020/12/15 18:00 | Wolverhampton v Chelsea | L | 2-1 |
| England Premier League | 2020/07/26 15:00 | Chelsea v Wolverhampton | W | 2-0 |
| England Premier League | 2023/12/30 12:30 | Luton v Chelsea | W | 2-3 |
| England Premier League | 2023/12/27 19:30 | Chelsea v Crystal Palace | W | 2-1 |
| England Premier League | 2023/12/24 13:00 | Wolverhampton v Chelsea | L | 2-1 |
| England EFL Cup | 2023/12/19 20:00 | Chelsea v Newcastle | D | 1-1 |
| England Premier League | 2023/12/16 15:00 | Chelsea v Sheff Utd | W | 2-0 |
| England Premier League | 2023/12/10 14:00 | Everton v Chelsea | L | 2-0 |
| England Premier League | 2023/12/06 20:15 | Man Utd v Chelsea | L | 2-1 |
| England Premier League | 2023/12/03 14:00 | Chelsea v Brighton | W | 3-2 |
| England Premier League | 2023/12/30 15:00 | Wolverhampton v Everton | W | 3-0 |
| England Premier League | 2023/12/27 19:30 | Brentford v Wolverhampton | W | 1-4 |
| England Premier League | 2023/12/24 13:00 | Wolverhampton v Chelsea | W | 2-1 |
| England Premier League | 2023/12/17 14:00 | West Ham v Wolverhampton | L | 3-0 |
| England Premier League | 2023/12/09 15:00 | Wolverhampton v Nottm Forest | D | 1-1 |
| England Premier League | 2023/12/05 19:30 | Wolverhampton v Burnley | W | 1-0 |
| England Premier League | 2023/12/02 15:00 | Arsenal v Wolverhampton | L | 2-1 |
| England Premier League | 2023/11/27 20:00 | Fulham v Wolverhampton | L | 3-2 |