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 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 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 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 |
| Australian Open | 2019/01/17 00:00 | Ivo Karlovic v Kei Nishikori | 3-6,6-7,7-5,7-5,6-7 |
| Australian Open | 2019/01/15 00:00 | Ivo Karlovic v Hubert Hurkacz | 6-7,7-6,7-6,7-6 |
| ATP Pune | 2019/01/05 11:30 | Kevin Anderson v Ivo Karlovic | 7-6,6-7,7-6 |
| ATP Pune | 2019/01/04 13:30 | Steve Darcis v Ivo Karlovic | 6-7,6-4,3-6 |