Head to Head
| European Tour 1 2021 | 2021/09/03 20:00 | Simon Whitlock v Darren Webster | 6-4 |
| PDC World Championship | 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 |
| PDC World Championship | 2016/12/23 19:15 | Darren Webster v Simon Whitlock | 4-0 |
| Players Championship Finals | 2016/11/26 13:40 | Simon Whitlock v Darren Webster | 3-6 |
Home History
| Players Championship 2 2023 | 2023/02/12 18:10 | Simon Whitlock v Danny Noppert | 3-8 |
| Players Championship 2 2023 | 2023/02/12 17:35 | Luke Humphries v Simon Whitlock | 4-7 |
| Players Championship 2 2023 | 2023/02/12 16:10 | Simon Whitlock v Raymond van Barneveld | 6-2 |
| PDC World Championship 2023 | 2022/12/19 16:05 | Jose De Sousa v Simon Whitlock | 3-2 |
| PDC World Championship 2023 | 2022/12/17 12:15 | Simon Whitlock v Christian Perez | 3-2 |
| Players Championship Finals 2022 | 2022/11/25 14:50 | Danny Noppert v Simon Whitlock | 6-1 |
| Grand Slam of Darts 2022 | 2022/11/16 19:15 | Raymond van Barneveld v Simon Whitlock | 10-8 |
| Grand Slam of Darts 2022 | 2022/11/14 20:10 | Simon Whitlock v Christian Perez | 5-3 |
Away History
| Players Championship 7 2022 | 2022/03/26 11:30 | Luc Peters v Darren Webster | 6-4 |
| Players Championship 6 2022 | 2022/03/20 12:30 | Ian White v Darren Webster | 6-1 |
| UK Open 2022 | 2022/03/04 12:10 | Darren Webster v Jose Justicia | 4-6 |
| Players Championship 4 2022 | 2022/02/13 12:25 | Ross Montgomery v Darren Webster | 3-6 |
| European Tour 1 2021 | 2021/09/03 20:00 | Simon Whitlock v Darren Webster | 6-4 |
| 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 |