| ITF Great Britain F2 | 2018/02/04 10:00 | Weightman, Oscar v Jack Gibbens | 6-1,6-4 |
| UK Pro League | 2021/07/16 10:00 | Weightman, Oscar v Liam Hignett | 7-6,6-4 |
| UK Pro League | 2021/07/15 11:30 | Lui Maxted v Weightman, Oscar | 6-3,6-3 |
| 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 |
| UK Pro League | 2021/07/16 13:00 | Jack Gibbens v Sean Hodkin | 6-4,6-7,10-3 |
| UK Pro League | 2021/07/15 09:00 | Cash, Julian v Jack Gibbens | 6-2,6-0 |
| UK Pro League | 2021/07/14 13:00 | Jack Gibbens v Lui Maxted | 7-6,3-6,2-10 |
| UK Pro League | 2021/07/12 11:15 | Alexis Canter v Jack Gibbens | 7-6,6-2 |
| ITF M25 The Hague | 2021/06/27 08:00 | van Nunen, Max v Jack Gibbens | 6-2,3-6,16-14 |
| ITF M25 Alkmaar | 2021/06/20 14:00 | Ivanov, Vladimir v Jack Gibbens | 6-2,7-5 |
| ITF - M15 Shymkent | 2021/06/02 05:00 | Tashbulatov, Dostanbek v Jack Gibbens | 6-2,6-3 |
| ITF - M15 Shymkent | 2021/06/01 05:00 | Edoardo Lavagno v Jack Gibbens | 6-4,6-2 |