Stadium: Court 10 Round: 44 Ground: Hardcourt outdoor
| ITF M25 Sintra | 2021/09/16 09:00 | Santiago Rodriguez Taverna v Jack Gibbens | 6-2,6-2 |
| ITF M25 Sintra | 2021/09/14 17:05 | Jack Gibbens v Stepan Pecak | 6-1,3-6,11-9 |
| UK Pro League | 2021/08/28 13:15 | Jack Gibbens v David Quayle | 7-6,6-1 |
| UK Pro League | 2021/08/27 14:30 | Jack Gibbens v Ewan Moore | 3-6,7-6,11-9 |
| UK Pro League | 2021/08/26 16:00 | Daniel Little v Jack Gibbens | 6-3,6-7,12-14 |
| UK Pro League | 2021/08/25 11:15 | Joshua Paris v Jack Gibbens | 6-1,7-5 |
| UK Pro League | 2021/08/24 10:00 | Billy Harris v Jack Gibbens | 6-2,6-2 |
| UK Pro League | 2021/07/18 15:43 | Jack Gibbens v Oscar Weightman | 3-6,6-4,0-0 |
| ITF M15 Monastir | 2021/09/08 08:00 | Takuto Niki v Lucca Pinto | 6-2,6-2 |
| ITF M15 Monastir | 2021/09/07 08:00 | Lucca Pinto v Mohamed Amin Oueslati | 6-2,6-3 |
| ITF M15 Monastir | 2021/08/29 10:30 | Adrian Arcon v Lucca Pinto | 6-3,6-4 |
| ITF M15 Monastir | 2021/08/22 12:00 | Lucca Pinto v Kai Lemstra | 3-6,0-6 |
| ITF M15 Monastir | 2021/08/16 07:30 | Jeremy Beale v Lucca Pinto | 6-2,6-0 |
| ITF M15 Monastir | 2021/08/15 07:30 | Lucca Pinto v Masood Eisa-Beygi | 6-1,6-0 |