Stadium: Court 17 Round: 23 Ground: Hardcourt outdoor
| ATP Tokyo | 2017/10/04 05:55 | Harrison, Ryan v Anderson, Kevin | 6-3,1-6,7-6 |
| ATP Stockholm | 2016/10/20 10:00 | Anderson, Kevin v Harrison, Ryan | 7-6,6-4 |
| Winston-Salem, USA | 2018/08/23 23:00 | Daniil Medvedev v Harrison, Ryan | 7-6,6-4 |
| Winston-Salem, USA | 2018/08/23 01:10 | Harrison, Ryan v Filip Krajinovic | 6-3,7-6 |
| Winston-Salem, USA | 2018/08/20 23:00 | Harrison, Ryan v Gojo, Borna | 6-2,6-4 |
| ATP Cincinnati Qual | 2018/08/12 00:30 | Harrison, Ryan v Hubert Hurkacz | 3-6,3-6 |
| Toronto, Canada | 2018/08/08 16:00 | Harrison, Ryan v Ilya Ivashka | 6-7,4-6 |
| Toronto, Canada | 2018/08/07 16:15 | Mackenzie McDonald v Harrison, Ryan | 4-6,2-6 |
| ATP Toronto Qual | 2018/08/05 15:00 | Harrison, Ryan v Mahut, Nicolas | 6-1,6-2 |
| ATP Toronto Qual | 2018/08/04 15:00 | Harrison, Ryan v Gulbis, Ernests | 6-3,7-6 |
| Cincinnati, USA | 2018/08/17 15:00 | Anderson, Kevin v David Goffin | 2-6,4-6 |
| Cincinnati, USA | 2018/08/15 17:35 | Anderson, Kevin v Chardy, Jérémy | 7-6,6-2 |
| Toronto, Canada | 2018/08/11 19:00 | Anderson, Kevin v Stefanos Tsitsipas | 7-6,4-6,6-7 |
| Toronto, Canada | 2018/08/10 16:30 | Grigor Dimitrov v Anderson, Kevin | 2-6,2-6 |
| Toronto, Canada | 2018/08/09 16:45 | Ilya Ivashka v Anderson, Kevin | 5-7,3-6 |
| Toronto, Canada | 2018/08/08 21:00 | Evgeny Donskoy v Anderson, Kevin | 6-4,2-6,6-7 |
| Wimbledon, London, Great Britain | 2018/07/15 13:00 | Anderson, Kevin v Novak Djokovic | 2-6,2-6,6-7 |
| Wimbledon, London, Great Britain | 2018/07/13 12:00 | Anderson, Kevin v Isner, John | 7-6,6-7,6-7,6-4,26-24 |