| Challenger de Cary | 09/13 22:30 | 27 | [186] Michael Mmoh v Tommy Paul [92] | 2-6,7-6,6-1 | |
| Challenger de Cary | 09/12 15:45 | 26 | Brandon Nakashima v Tommy Paul | 6-7,4-6 | |
| Challenger de Cary | 09/11 19:55 | 25 | [378] Ryan Peniston v Tommy Paul [92] | 4-6,6-7 | |
| Challenger de New Haven | 09/08 15:30 | 29 | [114] Tommy Paul v Marcos Giron [151] | 6-3,6-3 | |
| Challenger de New Haven | 09/07 16:15 | 28 | [195] Noah Rubin v Tommy Paul [114] | 0-6,6-7 | |
| Challenger de New Haven | 09/06 14:00 | 27 | [108] Bradley Klahn v Tommy Paul [114] | 4-6,4-6 | |
| Challenger de New Haven | 09/05 14:00 | 26 | [368] Sekou Bangoura v Tommy Paul [114] | 1-6,5-7 | |
| Challenger de New Haven | 09/04 14:00 | 25 | [204] Thai-Son Kwiatkowski v Tommy Paul [114] | 6-7,4-6 | |
| US Open | 08/21 19:40 | 45 | [112] Tommy Paul v Pedro Martinez [152] | 4-6,4-6 | |
| US Open | 08/19 15:00 | 44 | [112] Tommy Paul v Yannick Hanfmann [182] | 4-6,6-4,7-6 | |
| ATP Montreal | 08/08 01:15 | 25 | [128] Tommy Paul v Fabio Fognini [11] | 6-7,3-6 | |
| ATP Montreal | 08/05 17:25 | 24 | [128] Tommy Paul v Brayden Schnur [98] | 6-1,6-2 | |
| ATP Montreal | 08/04 16:35 | 46 | [78] Ricardas Berankis v Tommy Paul [128] | 6-4,6-7,3-6 | |
| ATP Montreal | 08/03 17:00 | 45 | [128] Tommy Paul v Alexei Popyrin [87] | 6-4,5-7,6-4 | |
| ATP Washington | 07/31 23:00 | 25 | [6] Stefanos Tsitsipas v Tommy Paul [128] | 6-3,7-5 | |
| ATP Washington | 07/29 18:00 | 24 | [98] Denis Kudla v Tommy Paul [128] | 0-6,4-6 | |
| ATP Atlanta | 07/21 22:30 | 164 | [102] Kamil Majchrzak v Tommy Paul [129] | 7-6,6-4 | |
| ATP Atlanta | 07/21 15:00 | 64 | [165] Michael Mmoh v Tommy Paul [129] | 7-5,6-7,6-7 | |
| Wimbledon | 06/27 10:00 | - | [108] Jiri Vesely v Tommy Paul [136] | 6-2,6-3,6-3 | |
| Wimbledon | 06/26 12:35 | 45 | [172] Mikael Torpegaard v Tommy Paul [136] | 6-0,4-6,4-6 | |
| Wimbledon | 06/24 10:00 | 44 | [429] Chun Hsin Tseng v Tommy Paul [136] | 3-6,3-6 | |
| ATP Queens | 06/16 11:35 | 164 | [85] Alexander Bublik v Tommy Paul [138] | 6-4,7-6 | |
| ATP Queens | 06/15 10:00 | 64 | [138] Tommy Paul v Bradley Klahn [89] | 6-1,6-4 | |
| ATP Hertogenbosch | 06/10 12:10 | 25 | [62] Jordan Thompson v Tommy Paul [138] | 3-6,6-1,6-4 | |
| ATP Hertogenbosch | 06/09 11:40 | 164 | [182] Daniel Brands v Tommy Paul [131] | 5-7,4-6 | |
| ATP Hertogenbosch | 06/08 14:50 | 64 | [155] Egor Gerasimov v Tommy Paul [131] | 4-6,3-6 | |
| Challenger de Surbiton | 06/05 09:30 | 25 | [84] Bernard Tomic v Tommy Paul [131] | 6-4,3-6,6-3 | |
| Challenger de Surbiton | 06/03 16:00 | 24 | [167] Filip Horansky v Tommy Paul [131] | 4-6,7-6,4-6 | |
| Open de Francia | 05/27 16:20 | 23 | [4] Dominic Thiem v Tommy Paul [131] | 6-4,4-6,7-6,6-2 | |
| ATP Ginebra | 05/19 09:00 | 164 | [58] Damir Dzumhur v Tommy Paul [133] | 6-2,4-6,6-3 |