| ATP Geneva | 05/19 09:00 | 164 | [58] Damir Dzumhur v Tommy Paul [133] | 6-2,4-6,6-3 | |
| ATP Geneva | 05/18 08:00 | 64 | [282] Stephane Robert v Tommy Paul [133] | 4-6,5-7 | |
| Challenger Savannah | 05/03 16:40 | 27 | Aleksandar Vukic v Tommy Paul | Walkover | |
| Challenger Savannah | 05/02 18:35 | 26 | [409] Alejandro Gonzalez v Tommy Paul [143] | 6-4,6-7,5-7 | |
| Challenger Savannah | 05/01 22:00 | 25 | [489] Sandro Ehrat v Tommy Paul [143] | 7-5,3-6,4-6 | |
| Challenger Tallahassee | 04/28 16:00 | 29 | [251] Emilio Gomez v Tommy Paul [158] | 6-2,6-2 | |
| Challenger Tallahassee | 04/27 15:35 | 28 | [158] Tommy Paul v Tennys Sandgren [103] | 6-4,6-3 | |
| Challenger Tallahassee | 04/26 20:40 | 27 | [158] Tommy Paul v Mikael Torpegaard [229] | 6-4,6-1 | |
| Challenger Tallahassee | 04/25 23:15 | 26 | [175] Mitchell Krueger v Tommy Paul [158] | 6-2,4-6,6-7 | |
| Challenger Tallahassee | 04/24 16:25 | 25 | [301] Martin Cuevas v Tommy Paul [158] | 1-6,4-6 | |
| Challenger Sarasota | 04/21 14:30 | 29 | [204] Tommy Paul v Tennys Sandgren [111] | 6-3,6-4 | |
| Challenger Sarasota | 04/20 18:05 | 28 | [341] Andrea Collarini v Tommy Paul [204] | 1-6,3-6 | |
| Challenger Sarasota | 04/19 14:00 | 27 | [204] Tommy Paul v Paolo Lorenzi [110] | 6-3,4-6,6-4 | |
| Challenger Sarasota | 04/18 16:30 | 26 | [201] Daniel Elahi Galan v Tommy Paul [204] | 6-2,1-6,1-6 | |
| Challenger Sarasota | 04/16 18:15 | 25 | [302] Gastao Elias v Tommy Paul [204] | 1-6,2-6 | |
| ATP Houston | 04/06 16:15 | 64 | [126] Henri Laaksonen v Tommy Paul [200] | 6-4,6-7,6-4 | |
| Australian Open | 01/10 02:25 | 45 | [109] Paolo Lorenzi v Tommy Paul [195] | 7-6,4-6,6-3 | |
| Australian Open | 01/08 23:00 | 44 | [195] Tommy Paul v Roberto Cid Subervi [249] | 6-4,6-3 | |
| Challenger Playford | 01/04 01:20 | 27 | [202] Tommy Paul v Zhe Li [277] | Retired | |
| Challenger Playford | 01/03 00:55 | 26 | [191] Hiroki Moriya v Tommy Paul [202] | 0-6,6-2,2-6 | |
| Challenger Playford | 12/31 23:30 | 25 | [202] Tommy Paul v Alexander Bublik [162] | 1-6,6-4,7-5 | |
| Challenger Playford | 12/30 23:30 | 24 | [200] Tommy Paul v Alexander Zhurbin [329] | 6-3,6-2 | |
| Challenger Champaign | 11/16 20:50 | 28 | [116] Reilly Opelka v Tommy Paul [215] | 2-6,6-4,6-4 | |
| Challenger Champaign | 11/15 21:15 | 27 | [176] Christopher Eubanks v Tommy Paul [215] | 2-6,6-7 | |
| Challenger Champaign | 11/15 01:20 | 26 | [440] Jared Hiltzik v Tommy Paul [215] | 6-7,4-6 | |
| Challenger Champaign | 11/12 20:40 | 25 | [215] Tommy Paul v Ugo Humbert [98] | 6-4,4-6,6-2 | |
| Challenger Knoxville | 11/07 16:35 | 25 | [222] Tommy Paul v Bjorn Fratangelo [131] | 4-6,4-6 | |
| Challenger Charlottesville | 11/04 20:00 | 29 | [277] Tommy Paul v Peter Polansky [130] | 6-2,6-2 | |
| Challenger Charlottesville | 11/03 18:40 | 28 | [101] Bradley Klahn v Tommy Paul [277] | 3-6,3-6 | |
| Challenger Charlottesville | 11/02 22:10 | 27 | [107] Ivo Karlovic v Tommy Paul [277] | 6-7,4-6 |