Stadium: Court 07 Round: 44 Ground: Hardcourt outdoor
| ITF M15 Monastir | 2020/12/14 09:30 | Osgar O'Hoisin v Jack Gibbens | 6-4,6-3 |
| ITF - M15 Cancún | 2021/09/26 15:00 | Jack Gibbens v Lucca Pinto | 5-7,6-3,10-2 |
| 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 |
| ITF - M15 Cancún | 2021/09/26 15:00 | Babji Siva Atturu v Osgar O'Hoisin | 1-6,0-6 |
| ITF - M15 Cancún | 2021/09/25 18:05 | Osgar O'Hoisin v Gerardo L Villasenor | 4-6,2-6 |
| ITF - M15 Cancún | 2021/09/24 19:30 | Osgar O'Hoisin v Leonardo Civita-Telles | 7-5,2-6,7-5 |
| ITF - M15 Cancún | 2021/09/23 19:15 | Jonas Maier v Osgar O'Hoisin | 6-3,4-6,4-6 |
| ITF - M15 Cancún | 2021/09/22 20:25 | Luciano Doria v Osgar O'Hoisin | 4-6,2-6 |
| ITF - M15 Cancún | 2021/09/21 14:00 | Emil Reinberg v Osgar O'Hoisin | 6-3,6-3 |
| ITF M25 Champaign | 2021/09/14 17:00 | Perry Gregg v Osgar O'Hoisin | 6-2,6-3 |
| UTR Pro Tennis Series - Barcelona | 2021/08/08 08:30 | Olexiy Kolisnyk v Osgar O'Hoisin | 7-6,3-6,5-2 |