Round: 62 Ground: Hardcourt outdoor
| ITF USA F5 | 2016/01/22 19:00 | Hunter Callahan v Jack Oswald | 6-1,6-1 |
| ITF USA F4 | 2016/01/15 13:30 | Jack Oswald v Rudy Richter | 4-6,1-6 |
| ITF Indonesia F5 | 2015/12/12 09:30 | Bogdan Didenko v Jack Oswald | 6-2,6-4 |
| ITF Tunisia F33 | 2015/11/22 12:00 | Jack Oswald v Alexey Prokopchuk | 1-6,2-6 |
| ITF Tunisia F31 | 2015/11/07 09:00 | Jack Oswald v James Allemby | 4-6,0-6 |
| ITF Zimbabwe F1 Qual | 2015/06/14 09:00 | Agustin Moyano v Jack Oswald | 6-3,4-6,6-3 |
| ITF Mozambique F1 | 2015/05/31 08:00 | Tomas Gerini v Jack Oswald | 6-0,6-3 |
| ITF Egypt F33 | 2015/04/19 10:00 | Nino Portales v Jack Oswald | 6-1,6-1 |