Stadium: Cancha 1 Round: 24 Ground: Hardcourt outdoor
| Drummondville, Canada | 2019/03/11 18:45 | Redlicki, Michael v Smith, Roy | 6-1,6-1 |
| Challenger Yokohama | 2019/02/25 02:30 | Kaichi Uchida v Smith, Roy | 6-3,6-3 |
| New York, USA | 2019/02/10 21:20 | Ramkumar Ramanathan v Smith, Roy | 4-6,6-2,6-4 |
| Challenger - Cleveland | 2019/01/30 02:55 | Smith, Roy v Young, Donald | 6-4,0-6,7-6 |
| Challenger - Cleveland | 2019/01/28 18:25 | Smith, Roy v Gijs Brouwer | 7-6,6-3 |
| Newport Beach, USA | 2019/01/21 19:30 | Smith, Roy v Benjamin Bonzi | 2-6,5-7 |
| Challenger Canberra | 2019/01/07 04:15 | Tomas Barrios Vera v Smith, Roy | 7-6,6-3 |
| Challenger Noumea | 2018/12/31 06:15 | Marc-Andrea Huesler v Smith, Roy | 6-4,7-6 |
| ATP - Miami | 2019/03/22 22:45 | Bautista-Agut, Roberto v Tipsarevic, Janko | 7-6,6-4 |
| ATP - Miami | 2019/03/20 18:50 | Tipsarevic, Janko v Klahn, Bradley | 6-3,6-3 |
| Bangkok, Thaïlande | 2019/02/14 06:15 | James Duckworth v Tipsarevic, Janko | 4-6,6-3,6-2 |
| Bangkok, Thaïlande | 2019/02/13 04:50 | Tipsarevic, Janko v Marc Polmans | 6-2,3-6,6-3 |
| Bangkok, Thaïlande | 2019/02/12 04:10 | Yang, Tsung-Hua v Tipsarevic, Janko | 2-6,6-4,4-6 |
| Open d'Australie | 2019/01/14 01:35 | Grigor Dimitrov v Tipsarevic, Janko | 4-6,6-3,6-1,6-4 |
| Kooyong Classic | 2019/01/08 02:35 | Jason Kubler v Tipsarevic, Janko | 4-6,6-3,10-12 |
| US Open, New York, USA | 2017/08/30 23:05 | Diego Schwartzman v Tipsarevic, Janko | 6-2,6-4,7-5 |