Stadium: Pista 1 Round: 54 Ground: Hardcourt outdoor
| ITF M25 Bakio | 2019/07/01 11:45 | Pablo Riva v Sergio Barranco | 4-6,1-6 |
| ITF M25 Glasgow | 2020/02/16 16:25 | Jack Oswald v Hendrik Jebens | 2-6,1-6 |
| ITF M25 Barnstaple | 2020/02/09 12:55 | Sean Hodkin v Jack Oswald | 6-2,6-3 |
| ITF M25 Shrewsbury | 2019/09/23 14:20 | Sizya Ernest Kivanda v Jack Oswald | 7-5,6-2 |
| ITF M25 Shrewsbury | 2019/09/23 10:10 | Andrew Ponder v Jack Oswald | 6-7,4-6 |
| ITF M25 Irpin | 2019/08/25 07:30 | Artur Kulibaba v Jack Oswald | 6-4,6-4 |
| ITF M25 Dublin | 2019/07/29 13:00 | Jack Oswald v Kyle Stocker | 0-6,4-6 |
| ITF M25 Lima | 2019/07/16 14:00 | Jack Oswald v Duilio Vallebuona | 3-6,2-6 |
| ITF M15 Lima | 2019/07/09 16:30 | Jack Oswald v Rodrigo N M D O Murillo | 3-6,4-6 |