| ITF M15 Weston | 07/01 13:00 | 25 | Ryan Harrison v Tom Jomby | 6-2,6-2 | |
| Challenger Orlando | 06/06 14:00 | 14 | [223] Ryan Harrison v Nick Chappell [360] | 2-6,6-7 | |
| Challenger Little Rock | 05/31 21:00 | 25 | [317] Goncalo Oliveira v Ryan Harrison [223] | 7-5,7-6 | |
| Challenger Tallahassee | 04/21 19:00 | 26 | [224] Ryan Harrison v Michael Mmoh [173] | 4-6,3-6 | |
| Challenger Tallahassee | 04/20 14:00 | 25 | [224] Ryan Harrison v Donald Young [346] | 2-6,6-3,6-3 | |
| Challenger Tallahassee | 04/20 14:00 | 25 | Ryan Harrison v Matthew Ebden | Cancelled | |
| ATP Delray Beach | 01/07 19:30 | 25 | [101] Gianluca Mager v Ryan Harrison [481] | 3-6,6-1,6-4 | |
| ATP Acapulco | 02/23 01:00 | 64 | [221] Daniel Altmaier v Ryan Harrison [433] | 6-2,6-3 | |
| ATP Acapulco | 02/23 00:35 | 64 | Cameron Norrie v Ryan Harrison | Cancelled | |
| ATP Delray Beach | 02/19 17:30 | 26 | [82] Soonwoo Kwon v Ryan Harrison [433] | 6-4,3-6,7-6 | |
| ATP Delray Beach | 02/17 17:45 | 25 | [433] Ryan Harrison v Damir Dzumhur [108] | 6-3,6-2 | |
| Challenger Cleveland | 02/13 19:55 | 26 | [280] Geoffrey Blancaneaux v Ryan Harrison [392] | 6-3,3-6,6-2 | |
| Challenger Cleveland | 02/13 00:05 | 25 | [392] Ryan Harrison v Sebastian Ofner [158] | 6-3,6-7,6-3 | |
| Challenger Cleveland | 02/10 23:00 | 24 | [392] Ryan Harrison v Collin Altamirano [385] | 6-4,7-6 | |
| Challenger Dallas | 02/04 03:00 | 24 | [394] Ryan Harrison v Brandon Nakashima [306] | 3-6,4-6 | |
| Challenger Newport Beach | 01/27 19:35 | 24 | [377] Michael Redlicki v Ryan Harrison [304] | 7-5,6-2 | |
| US Open | 08/19 16:15 | 44 | [113] Dominik Koepfer v Ryan Harrison [240] | 6-1,6-1 | |
| Challenger Aptos | 08/06 01:00 | 24 | [198] Ryan Harrison v Alexander Sarkissian [465] | Retired | |
| ATP Atlanta | 07/21 19:45 | 164 | [406] Kevin King v Ryan Harrison [136] | Retired | |
| ATP Atlanta | 07/21 18:20 | 64 | [167] Viktor Troicki v Ryan Harrison [136] | 6-4,5-7,6-7 | |
| French Open | 05/21 09:35 | 44 | [122] Ryan Harrison v Adam Pavlasek [248] | 3-6,7-6,6-7 | |
| ATP Houston | 04/10 18:05 | 26 | [126] Henri Laaksonen v Ryan Harrison [107] | 6-4,7-5 | |
| ATP Houston | 04/08 20:00 | 25 | [107] Ryan Harrison v Ivo Karlovic [77] | 6-3,6-4 | |
| ATP Miami | 03/18 18:20 | 44 | [198] Mikael Ymer v Ryan Harrison [104] | 6-1,6-3 | |
| Challenger Phoenix | 03/14 19:50 | 26 | [104] Ryan Harrison v Lorenzo Sonego [107] | 4-6,2-6 | |
| Challenger Phoenix | 03/13 22:05 | 25 | [92] Lloyd Harris v Ryan Harrison [104] | 6-3,4-6,4-6 | |
| Challenger Phoenix | 03/11 19:55 | 24 | [147] Gianluigi Quinzi v Ryan Harrison [104] | Retired | |
| ATP Indian Wells | 03/09 02:15 | 23 | [111] Roberto Carballes Baena v Ryan Harrison [104] | 6-3,7-5 | |
| ATP Acapulco | 02/26 02:45 | 25 | [93] Ryan Harrison v Stan Wawrinka [42] | 4-6,6-7 | |
| ATP Acapulco | 02/25 02:15 | 164 | [92] Ryan Harrison v Adrian Menendez-Maceiras [144] | 6-2,6-4 |