| UK Pro League | 2021/04/08 13:00 | Weightman, Oscar v Lui Maxted | 1-6,0-6 |
| UK Pro League | 2021/07/14 13:00 | Jack Gibbens v Lui Maxted | 7-6,3-6,2-10 |
| UK Pro League | 2021/07/13 13:00 | Alexis Canter v Lui Maxted | 6-4,4-6,2-10 |
| Eastbourne, Great Britain | 2021/06/19 12:30 | Norbert Gombos v Lui Maxted | 6-4,7-6 |
| Challenger Nottingham Qual | 2021/06/13 13:20 | Kacper Zuk v Lui Maxted | 6-2,6-1 |
| UK Pro League | 2021/04/11 15:00 | Billy Harris v Lui Maxted | 5-7,2-6 |
| UK Pro League | 2021/04/10 14:30 | Lui Maxted v Findel-Hawkins, Jack | 6-4,6-7,10-6 |
| UK Pro League | 2021/04/09 11:30 | Anton Matusevich v Lui Maxted | 6-4,6-4 |
| UK Pro League | 2021/04/08 13:00 | Weightman, Oscar v Lui Maxted | 1-6,0-6 |
| UK Pro League | 2021/07/14 10:00 | Weightman, Oscar v Hands, Tom | 6-3,6-3 |
| UK Pro League | 2021/07/12 10:00 | Cash, Julian v Weightman, Oscar | 6-7,6-4,10-6 |
| ITF - M15 Monastir | 2021/06/24 10:10 | Weightman, Oscar v Duckhee Lee | 3-6,7-6,3-6 |
| ITF - M15 Monastir | 2021/06/23 13:30 | Weightman, Oscar v Kelsey Stevenson | 1-6,7-5,7-5 |
| ITF - M15 Monastir | 2021/06/21 08:00 | Giles Hussey v Weightman, Oscar | 3-6,3-6 |
| ITF - M15 Monastir | 2021/06/20 09:00 | Noah Lopez v Weightman, Oscar | 6-7,0-6 |
| ITF - M15 Monastir | 2021/06/14 13:30 | Aidan Mayo v Weightman, Oscar | 6-2,4-6,10-7 |
| ITF - M15 Monastir | 2021/06/14 09:00 | Bruna, Esteban v Weightman, Oscar | 4-6,2-6 |