Stadium: Court 3 Round: 27 Ground: Hardcourt outdoor
| UK Pro League | 2023/01/02 11:30 | Samuel, Toby v George Loffhagen | 4-6,2-6 |
| ITF M25 Roehampton | 2023/08/02 12:20 | Samuel, Toby v Patrick Brady | 6-4,6-3 |
| ITF M25 Roehampton | 2023/08/01 14:30 | Samuel, Toby v Chen, Derrick | 6-2,6-1 |
| ITF - M25 Nottingham | 2023/07/15 09:30 | Billy Harris v Samuel, Toby | 4-6,4-6 |
| ITF - M25 Nottingham | 2023/07/14 10:00 | Samuel, Toby v Daniel Cox | 7-5,7-6 |
| ITF - M25 Nottingham | 2023/07/13 09:55 | Mats Rosenkranz v Samuel, Toby | 3-6,2-6 |
| ITF - M25 Nottingham | 2023/07/12 13:55 | Billy Blaydes v Samuel, Toby | 2-6,1-6 |
| ITF - M25 Nottingham | 2023/07/12 10:30 | Samuel, Toby v Luke Saville | 6-1,7-6 |
| Wimbledon, London, Great Britain | 2023/06/28 10:00 | Sho Shimabukuro v Samuel, Toby | 5-7,6-1,6-4 |
| ITF M25 Roehampton | 2023/08/02 10:00 | Badenhorst, Devin v George Loffhagen | 2-6,7-6,1-6 |
| ITF M25 Roehampton | 2023/08/01 10:35 | Finn Bass v George Loffhagen | 0-6,3-6 |
| Segovia, Spain | 2023/07/25 14:05 | Ricardas Berankis v George Loffhagen | 3-6,6-4,7-6 |
| Wimbledon, London, Great Britain | 2023/07/05 16:15 | George Loffhagen v Holger Rune | 6-7,3-6,2-6 |
| Eastbourne, Great Britain | 2023/06/26 14:50 | Luca Van Assche v George Loffhagen | 2-6,7-6,7-6 |
| Challenger - Nottingham | 2023/06/16 10:00 | Dominik Koepfer v George Loffhagen | 7-5,4-6,6-3 |
| Challenger - Nottingham | 2023/06/14 16:10 | George Loffhagen v Juncheng Shang | 6-4,5-7,6-3 |
| Challenger - Nottingham | 2023/06/13 17:30 | Otto Virtanen v George Loffhagen | 3-6,6-7 |