Stadium: Stadium Court Round: 25 Ground: Clay
| ATP - New York | 2018/02/15 20:00 | Ryan Harrison v Ivo Karlovic | 4-6,4-6 |
| ATP - Miami | 2019/03/18 18:20 | Mikael Ymer v Ryan Harrison | 6-1,6-3 |
| Challenger - Phoenix | 2019/03/14 19:50 | Ryan Harrison v Lorenzo Sonego | 4-6,2-6 |
| Challenger - Phoenix | 2019/03/13 22:05 | Lloyd Harris v Ryan Harrison | 6-3,4-6,4-6 |
| ATP - Indian Wells | 2019/03/09 02:15 | Roberto Carballes Baena v Ryan Harrison | 6-3,7-5 |
| ATP - Acapulco | 2019/02/26 02:45 | Ryan Harrison v Stan Wawrinka | 4-6,6-7 |
| ATP - Acapulco | 2019/02/25 02:15 | Ryan Harrison v Adrian Menendez-Maceiras | 6-2,6-4 |
| ATP - Acapulco | 2019/02/23 23:20 | Ryan Harrison v Juan A H Serrano | 7-5,6-2 |
| ATP - New York | 2019/02/13 17:55 | Paolo Lorenzi v Ryan Harrison | 4-6,6-4,6-4 |
| ATP - Miami | 2019/03/22 00:05 | Pablo Andujar v Ivo Karlovic | 7-6,6-4 |
| ATP - Indian Wells | 2019/03/14 01:00 | Ivo Karlovic v Dominic Thiem | 4-6,3-6 |
| ATP - Indian Wells | 2019/03/11 19:45 | Ivo Karlovic v Prajnesh Gunneswaran | 6-3,7-6 |
| ATP - Indian Wells | 2019/03/09 20:45 | Borna Coric v Ivo Karlovic | 4-6,6-7 |
| ATP - Indian Wells | 2019/03/07 20:40 | Ivo Karlovic v Matthew Ebden | 7-6,7-6 |
| ATP - Delray Beach | 2019/02/19 16:00 | Radu Albot v Ivo Karlovic | 7-6,6-4 |
| ATP - New York | 2019/02/13 16:00 | Ivo Karlovic v Radu Albot | 7-6,6-7,6-7 |
| ATP - Montpellier | 2019/02/04 15:00 | Marcel Granollers v Ivo Karlovic | 7-6,6-7,7-6 |