Stadium: Grandstand Round: 64 Ground: Hardcourt outdoor
| ATP New York | 2019/02/13 17:55 | Paolo Lorenzi v Ryan Harrison | 4-6,6-4,6-4 |
| ATP New York | 2019/02/12 19:55 | Peter Polansky v Ryan Harrison | 3-6,4-6 |
| Australian Open | 2019/01/17 07:30 | Ryan Harrison v Daniil Medvedev | 3-6,3-6,3-6 |
| Australian Open | 2019/01/15 00:00 | Jiri Vesely v Ryan Harrison | 0-6,5-7,3-6 |
| ATP Sydney | 2019/01/07 11:45 | Ryan Harrison v Yoshihito Nishioka | 4-6,2-6 |
| ATP Brisbane | 2019/01/01 05:00 | Nick Kyrgios v Ryan Harrison | 7-6,5-7,7-6 |
| ATP Basel | 2018/10/22 18:40 | Marius Copil v Ryan Harrison | 6-2,7-6 |
| US Open | 2018/08/27 21:15 | Ryan Harrison v Kevin Anderson | 6-7,7-5,6-4,3-6,4-6 |
| ATP Acapulco Qual | 2018/02/25 01:35 | Ernesto Escobedo v Alejandro Hernandez | 6-0,6-3 |