Face à face
| The Wimbledon Club Squash Squared Open 2019 | 2019/05/13 19:00 | James Willstrop v Simpson, Chris | 3-2 |
| DPD Open | 2016/11/13 08:54 | James Willstrop v Simpson, Chris | 11-0 |
Home History
| International de Nantes 2019 | 2019/09/09 11:15 | Simpson, Chris v Coleman, Ben | 2-0 |
| British Open | 2019/05/20 18:15 | Fathi, Karim Ali v Simpson, Chris | 3-0 |
| The Wimbledon Club Squash Squared Open 2019 | 2019/05/13 19:00 | James Willstrop v Simpson, Chris | 3-2 |
| The Wimbledon Club Squash Squared Open 2019 | 2019/05/11 19:00 | Tuominen, Olli v Simpson, Chris | 0-3 |
| DPD Open | 2019/04/11 16:45 | Simpson, Chris v Mohamed ElShorbagy | 0-3 |
| DPD Open | 2019/04/09 18:45 | Richards, Tom v Simpson, Chris | 1-3 |
| Grasshopper Cup | 2019/03/26 19:30 | Simpson, Chris v Castagnet, Mathieu | 0-3 |
| DPD Open | 2019/02/24 18:45 | Mohamed Abouelghar v Simpson, Chris | 3-2 |
Away History
| British Open | 2019/05/21 19:00 | James Willstrop v Mohamed ElShorbagy | 0-3 |
| British Open | 2019/05/20 18:15 | James Willstrop v Ramit Tandon | 3-0 |
| The Wimbledon Club Squash Squared Open 2019 | 2019/05/15 18:00 | James Willstrop v Iker Pajares Bernabeu | 0-3 |
| The Wimbledon Club Squash Squared Open 2019 | 2019/05/14 18:00 | James Willstrop v Lucas Serme | 3-0 |
| The Wimbledon Club Squash Squared Open 2019 | 2019/05/13 19:00 | James Willstrop v Simpson, Chris | 3-2 |
| European Team Championships | 2019/05/04 12:30 | Iker Pajares Bernabeu v James Willstrop | 4-5 |
| European Team Championships | 2019/05/02 10:00 | James Willstrop v Lopez, Edmon | 5-2 |
| European Team Championships | 2019/05/01 16:00 | James Willstrop v Emyr Evans | 9-5 |
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