Stadium: Court 2 Round: 26 Ground: Hardcourt indoor
| ITF Great Britain F3 | 2017/02/14 12:30 | Glasspool, Lloyd v Simon, Tobias | 5-7,6-7 |
| Barnstaple, Singles Qualifying M-ITF-GBR-01A | 2019/02/12 10:00 | Grills, Jacob v Simon, Tobias | 6-7,3-6 |
| ITF M25 Oberentfelden | 2019/02/07 19:50 | Simon, Tobias v Ehrat, Sandro | 7-6,3-6,6-7 |
| ITF M25 Oberentfelden | 2019/02/05 16:00 | Simon, Tobias v Alexander Ritschard | 6-7,6-1,7-6 |
| ITF - M25 Nussloch | 2019/01/25 13:00 | Simon, Tobias v Erler, Alexander | 4-6,6-7 |
| ITF - M25 Nussloch | 2019/01/24 13:30 | Simon, Tobias v Ryan Peniston | 7-6,6-4 |
| ITF - M25 Nussloch | 2019/01/22 11:00 | Simon, Tobias v Heger, Tim | 6-3,6-4 |
| Challenger Canberra | 2019/01/07 03:00 | Hugo Grenier v Simon, Tobias | 6-4,6-7,6-4 |
| Challenger Canberra | 2019/01/06 00:10 | Evans, Thomas v Simon, Tobias | 3-6,2-6 |
| Barnstaple, Singles Qualifying M-ITF-GBR-01A | 2019/02/12 12:25 | Glasspool, Lloyd v Orlando Luz | 6-7,6-4,6-3 |
| ITF M25 Oberentfelden | 2019/02/09 14:45 | Glasspool, Lloyd v Ehrat, Sandro | 4-6,4-6 |
| ITF M25 Oberentfelden | 2019/02/08 17:50 | Elmar Ejupovic v Glasspool, Lloyd | 3-6,6-7 |
| ITF M25 Oberentfelden | 2019/02/07 15:00 | Mattia Bellucci v Glasspool, Lloyd | 7-6,5-7,0-6 |
| ITF M25 Oberentfelden | 2019/02/06 13:35 | Okala, Jules v Glasspool, Lloyd | 3-6,6-7 |
| ITF M25 Tucson | 2019/01/12 18:00 | Redlicki, Martin v Glasspool, Lloyd | 3-6,7-6,6-2 |
| ITF M25 Tucson | 2019/01/11 17:00 | Kobelt, Peter v Glasspool, Lloyd | 3-6,7-6,4-6 |
| ITF M25 Tucson | 2019/01/10 17:00 | Brooksby, Jenson v Glasspool, Lloyd | 3-6,2-6 |