Stadium: Court 11 Round: 45 Ground: Hardcourt outdoor
| US Open, New York, USA | 2018/08/21 22:55 | Moraing, Mats v Young, Donald | 2-6,6-7 |
| Washington, USA | 2018/08/02 00:20 | Young, Donald v Kei Nishikori | 3-6,4-6 |
| Washington, USA | 2018/07/31 23:00 | Stan Wawrinka v Young, Donald | 4-6,7-6,6-7 |
| ATP Washington Qual | 2018/07/28 15:10 | Thomas, Danny v Young, Donald | 6-7,6-4,2-6 |
| Atlanta, USA | 2018/07/26 16:00 | Ebden, Matthew v Young, Donald | 6-4,6-4 |
| Atlanta, USA | 2018/07/23 23:00 | Karlovic, Ivo v Young, Donald | 6-2,6-7,6-7 |
| Newport, USA | 2018/07/16 16:20 | Young, Donald v Vasek Pospisil | 6-7,1-6 |
| Winnetka, USA | 2018/07/10 20:55 | Darian King v Young, Donald | 6-3,5-7,6-1 |
| US Open, New York, USA | 2018/08/21 22:50 | Neuchrist, Maximilian v Bolelli, Simone | 5-7,7-5,5-7 |
| Pullach, Germany | 2018/08/06 13:05 | Bolelli, Simone v Sebastian Ofner | 3-6,4-6 |
| Challenger Padova | 2018/07/25 17:00 | Eremin, Edoardo v Bolelli, Simone | 6-1,3-6,6-2 |
| ATP Bastad | 2018/07/20 14:30 | Bolelli, Simone v Laaksonen, Henri | 6-3,2-6,4-6 |
| ATP Bastad | 2018/07/18 10:20 | Diego Schwartzman v Bolelli, Simone | 6-7,3-6 |
| ATP Bastad | 2018/07/17 11:35 | Roberto Carballes Baena v Bolelli, Simone | 6-4,3-6,4-6 |
| ATP Bastad Qual | 2018/07/16 09:00 | Bolelli, Simone v Galovic, Viktor | 6-4,6-2 |
| ATP Bastad Qual | 2018/07/15 09:40 | Bolelli, Simone v Pedro Martinez | 6-2,6-3 |