Head to Head
| BDO World Championship 2019 | 2017/12/27 12:45 | Simon Whitlock v Darren Webster | 1-4 |
| BDO World Championship 2019 | 2017/04/22 14:25 | Simon Whitlock v Darren Webster | 6-3 |
| BDO World Championship 2019 | 2016/12/23 19:15 | Darren Webster v Simon Whitlock | 4-0 |
| BDO World Championship 2019 | 2016/11/26 13:40 | Simon Whitlock v Darren Webster | 3-6 |
Home History
| Players Championship 22 2021 | 2021/08/03 11:10 | Jelle Klaasen v Simon Whitlock | 3-6 |
| Players Championship 21 2021 | 2021/08/02 13:10 | Daryl Gurney v Simon Whitlock | 6-5 |
| Players Championship 19 2021 | 2021/07/07 11:00 | Jonny Clayton v Simon Whitlock | 6-5 |
| Players Championship 14 2021 | 2021/06/15 14:20 | Lewy Williams v Simon Whitlock | 1-6 |
| Players Championship 13 2021 | 2021/06/14 13:55 | Ian White v Simon Whitlock | 6-5 |
| Players Championship 12 2021 | 2021/04/27 14:55 | Simon Whitlock v Dirk van Duijvenbode | 0-6 |
| Players Championship 12 2021 | 2021/04/27 13:35 | Michael van Gerwen v Simon Whitlock | 3-6 |
| Players Championship 12 2021 | 2021/04/27 12:20 | Vincent van der Voort v Simon Whitlock | 3-6 |
Away History
| Players Championship 20 2021 | 2021/07/08 12:15 | Derk Telnekes v Darren Webster | 3-6 |
| Players Championship 18 2021 | 2021/07/06 13:20 | Darren Webster v Ted Evetts | 3-6 |
| Players Championship 14 2021 | 2021/06/15 16:25 | Dimitri van den Bergh v Darren Webster | 6-1 |
| Players Championship 8 2021 | 2021/03/19 14:45 | Jose De Sousa v Darren Webster | 6-2 |
| PDC UK Open 2021 | 2021/03/05 20:30 | Darius Labanauskas v Darren Webster | 10-5 |
| PDC UK Open 2021 | 2021/03/05 13:50 | Ted Evetts v Darren Webster | 4-6 |
| Players Championship 3 2021 | 2021/02/27 14:45 | Brendan Dolan v Darren Webster | 6-3 |
| Players Championship Finals 2020 | 2020/11/27 21:45 | Darren Webster v Jeffrey de Zwaan | 3-6 |