| ITF USA F36 | 2016/11/07 15:30 | Oliver Crawford v Noe Khlif | 6-3,6-1 |
| ITF USA F8 | 2016/02/25 16:30 | Oliver Crawford v Jonathan Eysseric | 2-6,3-6 |
| ITF USA F8 | 2016/02/24 16:30 | Oliver Crawford v Peter Torebko | 6-3,0-6,7-6 |
| ITF USA F8 Qual | 2016/02/22 17:00 | Reilly Opelka v Oliver Crawford | 3-6,4-6 |
| ITF USA F8 Qual | 2016/02/21 17:00 | Oliver Crawford v Oscar Gabriel Ortiz | 6-2,6-4 |
| ITF USA F8 Qual | 2016/02/19 17:30 | Oliver Crawford v Oscar Matias Leiva Biason | 6-2,6-0 |
| ITF USA F7 Qual | 2016/02/13 17:00 | Gianni Ross v Oliver Crawford | 7-5,6-7,6-4 |
| ITF USA F7 Qual | 2016/02/12 15:30 | Oliver Crawford v Alexandre Rotsaert | 7-6,6-3 |
| ITF USA F35 | 2016/11/05 17:55 | Lukas Ollert v Felix Auger Aliassime | 6-7,2-6 |
| ITF USA F35 | 2016/11/04 15:00 | Benjamin Sigouin v Lukas Ollert | 4-6,6-2,2-6 |
| ITF USA F35 | 2016/11/03 18:15 | Lukas Ollert v Dominic Cotrone | 6-4,4-6,6-3 |
| ITF USA F35 | 2016/11/01 21:05 | Niclas Braun v Lukas Ollert | 0-6,6-4,0-6 |
| ITF Germany F15 | 2016/10/20 15:50 | Lukas Ollert v Rudolf Molleker | 3-6,4-6 |
| ITF Germany F15 | 2016/10/18 09:00 | Patrik Fabian v Lukas Ollert | 7-5,3-6,3-6 |
| ITF Germany F14 | 2016/10/11 11:10 | Marvin Moeller v Lukas Ollert | 6-0,6-2 |
| ITF Germany F14 | 2016/10/10 10:00 | Lukas Ollert v Kai Lemstra | 7-5,6-2 |