| ATP Acapulco | 02/27 23:00 | 27 | [20] John Isner v Tommy Paul [66] | 7-6,3-6,6-2 | |
| ATP Acapulco | 02/27 00:00 | 26 | [66] Tommy Paul v Alexander Zverev [7] | 6-3,6-4 | |
| ATP Acapulco | 02/25 00:15 | 25 | [66] Tommy Paul v Mackenzie McDonald [196] | 6-7,6-4,6-4 | |
| ATP Acapulco | 02/23 23:35 | 164 | [70] Tommy Paul v Daniel Elahi Galan [146] | 6-4,6-4 | |
| ATP Acapulco | 02/23 01:00 | 64 | [70] Tommy Paul v Danilo Petrovic [155] | Retired | |
| ATP Delray Beach | 02/20 19:35 | 26 | [70] Tommy Paul v Frances Tiafoe [84] | 5-7,6-7 | |
| ATP Delray Beach | 02/19 01:30 | 25 | [146] Daniel Elahi Galan v Tommy Paul [70] | 2-6,4-6 | |
| ATP Delray Beach | 02/19 01:00 | 25 | Nick Kyrgios v Tommy Paul | Cancelled | |
| ATP New York | 02/10 19:25 | 25 | [54] Miomir Kecmanovic v Tommy Paul [70] | 6-4,6-2 | |
| Australian Open | 01/24 01:45 | 25 | [67] Marton Fucsovics v Tommy Paul [80] | 6-1,6-1,6-4 | |
| Australian Open | 01/22 04:00 | 24 | [80] Tommy Paul v Grigor Dimitrov [20] | 6-4,7-6,3-6,6-7,7-6 | |
| Australian Open | 01/21 01:45 | 23 | [101] Leonardo Mayer v Tommy Paul [80] | 6-4,4-6,4-6,4-6 | |
| ATP Adelaide | 01/17 02:30 | 28 | [90] Tommy Paul v Lloyd Harris [91] | 4-6,7-6,3-6 | |
| ATP Adelaide | 01/16 04:10 | 27 | [42] Albert Ramos-Vinolas v Tommy Paul [90] | 3-6,4-6 | |
| ATP Adelaide | 01/15 02:40 | 26 | [90] Tommy Paul v Pablo Cuevas [44] | 6-1,6-2 | |
| ATP Adelaide | 01/14 00:30 | 25 | [54] Aljaz Bedene v Tommy Paul [90] | 4-6,4-6 | |
| ATP Adelaide | 01/12 06:40 | 164 | [77] Nicolas Jarry v Tommy Paul [90] | 3-6,2-6 | |
| ATP Adelaide | 01/11 06:15 | 64 | Matthew C Romios v Tommy Paul | 2-6,2-6 | |
| Challenger Knoxville | 11/09 17:55 | 28 | [90] Tommy Paul v Christopher O'Connell [140] | 6-7,3-6 | |
| Challenger Knoxville | 11/08 23:30 | 27 | [90] Tommy Paul v Blaz Rola [139] | 2-6,6-1,7-6 | |
| Challenger Knoxville | 11/07 22:30 | 26 | [90] Tommy Paul v Vasek Pospisil [153] | Retired | |
| Challenger Knoxville | 11/06 19:10 | 25 | [90] Tommy Paul v Evan King [348] | 6-2,6-7,7-6 | |
| ATP Stockholm | 10/15 12:40 | 25 | Tommy Paul v Pablo Andujar | Cancelled | |
| ATP Stockholm | 10/14 10:00 | 164 | Tommy Paul v Lucas Renard | 6-4,6-3 | |
| ATP Stockholm | 10/13 12:00 | 64 | Tommy Paul v Markus Eriksson | 6-1,6-1 | |
| Challenger Tiburon | 09/29 21:00 | 29 | [87] Tommy Paul v Thanasi Kokkinakis [183] | 7-5,6-7,6-4 | |
| Challenger Tiburon | 09/28 23:30 | 28 | [87] Tommy Paul v Emilio Gomez [158] | 6-1,7-6 | |
| Challenger Tiburon | 09/28 00:00 | 27 | [87] Tommy Paul v Gonzalo Escobar [355] | 6-4,1-6,7-6 | |
| Challenger Tiburon | 09/26 21:10 | 26 | [87] Tommy Paul v Hugo Gaston [379] | 7-6,6-1 | |
| Challenger Tiburon | 09/25 22:30 | 25 | Tommy Paul v Brandon Holt | 5-7,6-3,6-2 |