Round: 25 Ground: Clay
| ITF USA F36 | 2016/11/08 15:30 | Patrick Kypson v Sigouin, Benjamin | 7-6,1-6,4-6 |
| ITF USA F22 | 2016/06/29 17:30 | Patrick Kypson v Silverman, Cameron | 3-6,3-6 |
| ITF Netherlands F1 | 2016/06/14 14:35 | Patrick Kypson v Jose Pereira | 0-6,2-6 |
| ITF Netherlands F1 Qual | 2016/06/11 08:00 | Lucas Andriamasilalao v Patrick Kypson | 1-6,2-6 |
| ITF USA F8 | 2016/02/25 16:00 | Patrick Kypson v Noah Rubin | 5-7,7-5,3-6 |
| ITF USA F8 | 2016/02/23 17:00 | Heras, Patricio v Patrick Kypson | 2-6,7-5,3-6 |
| USA F7, Singles Qualifying | 2016/02/16 17:30 | Patrick Kypson v Mina, Gianni | 4-6,1-6 |
| ITF USA F6 | 2016/02/03 14:00 | King, Evan v Patrick Kypson | 6-3,7-6 |
| ITF USA F36 | 2016/11/08 17:00 | Maxime Chazal v Ross, Gianni | 6-3,6-1 |
| ITF USA F15 | 2016/04/28 17:35 | Ross, Gianni v Quiroz, Roberto | 7-6,4-6,5-7 |
| ITF USA F15 | 2016/04/27 14:00 | Nevolo, Dennis v Ross, Gianni | 3-6,3-6 |
| ITF USA F8 Qual | 2016/02/19 23:30 | Ross, Gianni v Matias Franco Descotte | 6-4,6-4 |
| ITF USA F7 Qual | 2016/02/14 17:00 | Nagy, Peter v Ross, Gianni | 6-1,6-2 |
| ITF USA F7 Qual | 2016/02/13 17:00 | Ross, Gianni v Oliver Crawford | 7-5,6-7,6-4 |
| ITF USA F7 Qual | 2016/02/12 15:30 | Ross, Gianni v Battistone, Brian | 6-2,6-4 |
| ITF USA F6 | 2016/02/01 14:30 | Nagy, Peter v Ross, Gianni | 6-4,6-4 |