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 |
| Challenger Morelos | 2019/02/19 16:00 | Renzo Olivo v Juan A H Serrano | 6-4,6-1 |
| ITF USA F35 | 2018/12/04 19:40 | Juan A H Serrano v Adam El Mihdawy | 5-7,4-6 |
| ITF USA F32 | 2018/11/16 16:00 | Juan A H Serrano v Nuno Borges | 2-6,1-6 |
| ITF USA F32 | 2018/11/15 18:30 | Juan I Cabrera v Juan A H Serrano | 2-6,3-6 |
| ITF USA F30 | 2018/11/08 18:30 | Juan A H Serrano v Trevor A Johnson | 6-7,0-6 |
| ITF USA F30 | 2018/11/07 16:45 | Juan A H Serrano v Roberts Grinvalds | 6-4,6-2 |
| ITF USA F28B | 2018/10/23 17:35 | Juan A H Serrano v Yshai Oliel | 0-6,2-6 |
| ITF USA F28B | 2018/10/22 17:05 | Juan A H Serrano v Pierce Rollins | 6-3,6-1 |