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