| St George's Hill Championships 2019 | 11/19 15:00 | 7 | Mazen Hesham v Simpson, Chris | 3-2 | |
| PSA World Championships | 11/08 16:00 | 7 | Simpson, Chris v Adrian Waller | 0-3 | |
| Egypt Open | 10/27 10:00 | 9 | Selby, Daryl v Simpson, Chris | 3-2 | |
| Egypt Open | 10/26 13:00 | 8 | Simpson, Chris v Mohamed Abouelghar | 3-2 | |
| Egypt Open | 10/25 10:00 | 7 | Simpson, Chris v Lopez, Edmon | Retired | |
| International de Nantes 2019 | 09/10 11:15 | 8 | Simpson, Chris v James Willstrop | 0-2 | |
| International de Nantes 2019 | 09/09 11:15 | 7 | Simpson, Chris v Coleman, Ben | 2-0 | |
| British Open 2019 | 05/20 18:15 | 7 | Fathi, Karim Ali v Simpson, Chris | 3-0 | |
| The Wimbledon Club Squash Squared Open 2019 | 05/13 19:00 | 8 | James Willstrop v Simpson, Chris | 3-2 | |
| The Wimbledon Club Squash Squared Open 2019 | 05/11 19:00 | 7 | Tuominen, Olli v Simpson, Chris | 0-3 | |
| DPD Open | 04/11 16:45 | 8 | Simpson, Chris v Mohamed ElShorbagy | 0-3 | |
| DPD Open | 04/09 18:45 | 7 | Richards, Tom v Simpson, Chris | 1-3 | |
| Grasshopper Cup | 03/26 19:30 | 7 | Simpson, Chris v Castagnet, Mathieu | 0-3 | |
| DPD Open | 02/24 18:45 | 8 | Mohamed Abouelghar v Simpson, Chris | 3-2 | |
| PSA World Championships | 02/23 18:45 | 7 | Shahjahan Khan v Simpson, Chris | 0-3 | |
| DPD Open | 02/15 16:00 | - | Selby, Daryl v Simpson, Chris | 9-6 | |
| DPD Open | 01/29 21:00 | 7 | Iker Pajares Bernabeu v Simpson, Chris | 3-2 | |
| DPD Open | 01/18 17:00 | 8 | Greg Lobban v Simpson, Chris | 3-0 | |
| DPD Open | 01/16 23:15 | 7 | Simpson, Chris v Golan, Borja | 3-1 | |
| DPD Open | 12/06 11:00 | 9 | Simpson, Chris v Paul Coll | 0-3 | |
| DPD Open | 12/05 12:00 | 8 | Salem, Zahed v Simpson, Chris | 2-3 | |
| DPD Open | 12/03 17:00 | 7 | Lopez, Edmon v Simpson, Chris | 0-3 | |
| DPD Open | 11/19 07:00 | 7 | Masters, Joshua v Simpson, Chris | 3-2 | |
| DPD Open | 11/11 14:30 | 8 | Simpson, Chris v Yuen, Ivan | 0-3 | |
| DPD Open | 10/27 09:00 | 7 | Simpson, Chris v Mazen Hesham | 1-3 | |
| DPD Open | 10/16 15:00 | 7 | Pilley, Cameron v Simpson, Chris | 3-0 | |
| DPD Open | 10/07 20:45 | 8 | Gaultier, Gregory v Simpson, Chris | 3-1 | |
| DPD Open | 10/06 20:45 | 7 | Simpson, Chris v Gregoire Marche | 3-2 | |
| DPD Open | 05/15 19:00 | 7 | Simpson, Chris v Ali Farag | 0-3 | |
| DPD Open | 05/14 15:30 | 1 | Simpson, Chris v Clyne, Alan | 3-0 |