| Challenger de Tallahassee | 04/15 19:20 | 25 | Calvin Hemery v Patrick Kypson | 7-6,6-3 | |
| Challenger de Sarasota | 04/08 20:50 | 25 | [277] Mitchell Krueger v Patrick Kypson [144] | 6-2,3-6,7-6 | |
| ATP Houston | 04/01 20:35 | 25 | [133] Patrick Kypson v Zizou Bergs [111] | 6-7,3-6 | |
| ATP Houston | 03/31 18:05 | 19 | [140] Patrick Kypson v Brandon Holt [288] | Retired | |
| ATP Houston | 03/30 20:10 | 14 | Patrick Kypson v Kiranpal Pannu | 6-2,6-2 | |
| ATP Miami | 03/18 16:45 | 14 | [98] Aleksandar Kovacevic v Patrick Kypson [140] | 6-2,7-6 | |
| ATP Indian Wells | 03/09 19:00 | 24 | [151] Patrick Kypson v Ugo Humbert [14] | 4-6,4-6 | |
| ATP Indian Wells | 03/08 01:50 | 23 | [284] Ethan Quinn v Patrick Kypson [151] | 1-6,6-7 | |
| ATP Delray Beach | 02/16 23:00 | 27 | [52] Marcos Giron v Patrick Kypson [155] | 6-4,6-4 | |
| ATP Delray Beach | 02/14 18:00 | 26 | [104] Constant Lestienne v Patrick Kypson [155] | 4-6,4-6 | |
| ATP Delray Beach | 02/13 01:10 | 25 | [155] Patrick Kypson v Miomir Kecmanovic [40] | 6-4,7-6 | |
| Challenger de Cleveland | 02/04 18:00 | 29 | [185] Patrick Kypson v Ethan Quinn [337] | 4-6,6-3,6-2 | |
| Challenger de Cleveland | 02/03 20:40 | 28 | [98] James Duckworth v Patrick Kypson [185] | 3-6,6-7 | |
| Challenger de Cleveland | 02/02 21:10 | 27 | [150] Emilio Nava v Patrick Kypson [185] | 6-4,6-7,4-6 | |
| Challenger de Cleveland | 01/31 17:35 | 26 | Murphy Cassone v Patrick Kypson | 4-6,6-7 | |
| Challenger de Cleveland | 01/30 00:15 | 25 | [496] Nathan Ponwith v Patrick Kypson [185] | 3-6,2-6 | |
| Open de Australia | 01/15 00:00 | 23 | [186] Patrick Kypson v Emil Ruusuvuori [50] | 6-4,3-6,4-6,6-7 | |
| ATP Auckland | 01/06 22:00 | 19 | [191] Patrick Kypson v Alejandro Tabilo [85] | 6-7,3-6 | |
| ATP Auckland | 01/05 22:00 | 14 | Jake Delaney v Patrick Kypson | 1-6,4-6 | |
| ATP Auckland | 01/05 22:00 | 14 | Taro Daniel v Patrick Kypson | Cancelled | |
| Challenger de Nouméa | 01/03 05:00 | 26 | [130] Arthur Cazaux v Patrick Kypson [191] | 3-6,7-6,6-2 | |
| Challenger de Nouméa | 01/02 01:30 | 25 | [191] Patrick Kypson v Blake Mott [407] | 6-3,7-5 | |
| Challenger de Champaign | 11/19 17:00 | 29 | [239] Patrick Kypson v Alex Michelsen [99] | 6-4,6-3 | |
| Challenger de Champaign | 11/18 21:45 | 28 | [239] Patrick Kypson v Ethan Quinn [374] | 6-4,6-2 | |
| Challenger de Champaign | 11/17 23:00 | 27 | [117] Aleksandar Kovacevic v Patrick Kypson [239] | 6-7,6-4,3-6 | |
| Challenger de Champaign | 11/16 00:35 | 26 | Kenta Miyoshi v Patrick Kypson | 3-6,1-6 | |
| Challenger de Champaign | 11/14 18:35 | 25 | [295] Mark Whitehouse v Patrick Kypson [239] | 1-6,6-7 | |
| Challenger de Knoxville | 11/07 15:00 | 25 | [183] Denis Kudla v Patrick Kypson [241] | 6-7,6-3,6-4 | |
| Challenger de Charlottesville | 11/04 17:30 | 28 | [247] Beibit Zhukayev v Patrick Kypson [254] | 6-4,7-6 | |
| Challenger de Charlottesville | 11/03 16:00 | 27 | [254] Patrick Kypson v Brandon Holt [285] | 6-1,6-4 |