[17] Wolverhampton 2-5 Chelsea [11] 2019-09-14 14:00
Stadium: Molineux Stadium Round: 5
Referee: Graham Scott Home Manager: Nuno Espirito Santo Away Manager: Frank Lampard
Head to Head
| England - Premier League | 2019/03/10 14:05 | Chelsea v Wolverhampton | D | 1-1 |
| England - Premier League | 2018/12/05 19:45 | Wolverhampton v Chelsea | W | 2-1 |
| England - FA-cupen | 2017/02/18 17:30 | Wolverhampton v Chelsea | L | 0-2 |
Home History
| England - Premier League | 2019/09/01 13:00 | Everton v Wolverhampton | L | 3-2 |
| UEFA Europa League - Kval | 2019/08/29 18:45 | Wolverhampton v Torino | W | 2-1 |
| England - Premier League | 2019/08/25 15:30 | Wolverhampton v Burnley | D | 1-1 |
| UEFA Europa League - Kval | 2019/08/22 19:00 | Torino v Wolverhampton | W | 2-3 |
| England - Premier League | 2019/08/19 19:00 | Wolverhampton v Man Utd | D | 1-1 |
| UEFA Europa League - Kval | 2019/08/15 18:45 | Wolverhampton v Pyunik Yerevan | W | 4-0 |
| England - Premier League | 2019/08/11 13:00 | Leicester v Wolverhampton | D | 0-0 |
| UEFA Europa League - Kval | 2019/08/08 16:00 | Pyunik Yerevan v Wolverhampton | W | 0-4 |
Away History
| England - Premier League | 2019/08/31 14:00 | Chelsea v Sheff Utd | D | 2-2 |
| England - Premier League | 2019/08/24 11:30 | Norwich v Chelsea | W | 2-3 |
| England - Premier League | 2019/08/18 15:30 | Chelsea v Leicester | D | 1-1 |
| UEFA Super Cup | 2019/08/14 19:00 | Liverpool v Chelsea | L | 7-6 |
| England - Premier League | 2019/08/11 15:30 | Man Utd v Chelsea | L | 4-0 |
| Europa - Vänskapsmatcher | 2019/08/03 15:00 | Borussia M'gladbach v Chelsea | D | 2-2 |
| Europa - Vänskapsmatcher | 2019/07/31 18:00 | FC Salzburg v Chelsea | W | 3-5 |
| Europa - Vänskapsmatcher | 2019/07/28 14:00 | Reading v Chelsea | W | 3-4 |