Stadium: Court 16 Round: 25 Ground: Hardcourt outdoor
| ITF - M15 Heraklion | 2023/10/17 06:30 | Guy Den Ouden v David Quayle | 6-1,7-5 |
| ITF - M15 Heraklion | 2023/10/16 07:00 | Eleftherios Neos v David Quayle | 3-6,4-6 |
| UK Pro League | 2023/10/07 13:00 | David Quayle v Sean Hodkin | 2-6,1-6 |
| UK Pro League | 2023/10/06 10:00 | David Quayle v George Houghton | 2-6,4-6 |
| UK Pro League | 2023/10/05 10:00 | Brandon Murphy v David Quayle | 4-6,2-6 |
| UK Pro League | 2023/10/04 10:00 | Harry Wendelken v David Quayle | 3-6,6-1,11-9 |
| UK Pro League | 2023/10/02 13:00 | Ivan Denisov v David Quayle | 6-4,6-2 |
| ITF - M15 Sharm-el-Sheikh | 2023/09/28 09:55 | David Quayle v Stuart Parker | 4-6,6-7 |
| ITF - M25 Falun | 2023/09/25 07:50 | Johannes Ingildsen v Oliver Ojakaar | 6-2,6-2 |
| ITF - M25 Falun | 2023/09/24 08:00 | Filip Stidell v Oliver Ojakaar | 1-6,2-6 |
| ITF - M15 Danderyd | 2023/09/20 12:25 | Oliver Ojakaar v Mats Rosenkranz | 4-6,6-4,3-6 |
| ITF - M15 Krsko | 2023/05/19 11:30 | Lucas Gerch v Oliver Ojakaar | 1-6,6-3,6-4 |
| ITF - M15 Krsko | 2023/05/19 08:00 | Oliver Ojakaar v Gergely Madarasz | 7-5,6-1 |
| ITF - M15 Krsko | 2023/05/18 10:25 | Matic Dimic v Oliver Ojakaar | 3-6,4-6 |
| ITF - M15 Doha | 2021/12/15 16:25 | Ryan James Storrie v Oliver Ojakaar | 7-6,6-2 |
| ITF - M15 Doha | 2021/12/14 14:05 | Oliver Ojakaar v Cheraag Bajwa | 2-6,6-1,10-4 |