| Wimbledon, London, Great Britain | 07/02 16:00 | 23 | Harrison, Ryan v Roberto Carballes Baena | 6-1,6-4,6-2 | |
| Eastbourne, Great Britain | 06/25 12:40 | 25 | [223] Jay Clarke v Harrison, Ryan [58] | 6-4,6-1 | |
| London, Great Britain | 06/19 17:45 | 25 | [58] Harrison, Ryan v Kyle Edmund [17] | 6-7,4-6 | |
| French Open, Paris, France | 05/29 09:00 | 23 | [56] Harrison, Ryan v Maximilian Marterer [70] | 1-6,3-6,5-7 | |
| Geneva, Switzerland | 05/21 16:00 | 25 | [61] Frances Tiafoe v Harrison, Ryan [56] | 3-6,7-6,6-4 | |
| ATP - Rome | 05/15 20:25 | 25 | [57] Harrison, Ryan v Marin Cilic [5] | 7-6,1-6,6-7 | |
| ATP - Rome | 05/13 12:40 | 24 | [59] Harrison, Ryan v Sugita, Yuichi [46] | 7-6,6-3 | |
| ATP - Madrid | 05/09 14:25 | 25 | [9] Isner, John v Harrison, Ryan [59] | 7-6,7-6 | |
| ATP - Madrid | 05/08 16:15 | 24 | [69] Garcia-Lopez, Guillermo v Harrison, Ryan [59] | 4-6,6-7 | |
| ATP - Houston | 04/12 18:35 | 26 | [72] Taylor Fritz v Harrison, Ryan [54] | 3-6,6-0,6-3 | |
| ATP - Houston | 04/10 20:35 | 25 | [187] Miomir Kecmanovic v Harrison, Ryan [54] | 4-6,3-6 | |
| Coupe Davis | 04/08 19:00 | 27 | [54] Harrison, Ryan v Bemelmans, Ruben [110] | 6-3,6-4 | |
| ATP - Miami | 03/21 15:00 | 23 | [53] Harrison, Ryan v Joao Sousa [80] | 6-7,6-7 | |
| ATP - Indian Wells | 03/09 01:05 | 23 | Harrison, Ryan v Delbonis, Federico | 2-6,6-4,5-7 | |
| ATP - Acapulco | 03/01 23:30 | 27 | Harrison, Ryan v Alexander Zverev | 4-6,1-6 | |
| ATP - Acapulco | 02/28 23:30 | 26 | Harrison, Ryan v Diego Schwartzman | 6-3,5-7,6-4 | |
| ATP - Acapulco | 02/27 01:00 | 25 | Isner, John v Harrison, Ryan | 3-6,6-7 | |
| ATP - Delray Beach | 02/20 16:00 | 25 | Opelka, Reilly v Harrison, Ryan | 7-6,7-6 | |
| New York, USA | 02/15 20:00 | 26 | Harrison, Ryan v Karlovic, Ivo | 4-6,4-6 | |
| New York, USA | 02/13 00:30 | 25 | Harrison, Ryan v Young, Donald | 6-3,7-6 | |
| Open d'Australie | 01/19 09:00 | 25 | Harrison, Ryan v Marin Cilic | 6-7,3-6,6-7 | |
| Open d'Australie | 01/17 04:15 | 24 | Cuevas, Pablo v Harrison, Ryan | 4-6,6-7,4-6 | |
| Open d'Australie | 01/15 00:00 | 23 | Sela, Dudi v Harrison, Ryan | 3-6,7-5,6-3,5-7,2-6 | |
| ATP - Auckland | 01/09 00:50 | 25 | Steve Johnson v Harrison, Ryan | Cancelled | |
| ATP Brisbane | 01/07 09:00 | 29 | Kyrgios, Nick v Harrison, Ryan | 6-4,6-2 | |
| ATP Brisbane | 01/06 03:20 | 28 | Alex De Minaur v Harrison, Ryan | 6-4,6-7,4-6 | |
| ATP Brisbane | 01/05 04:20 | 27 | Istomin, Denis v Harrison, Ryan | Retired | |
| ATP Brisbane | 01/04 05:15 | 26 | Harrison, Ryan v Yannick Hanfmann | 6-7,6-4,6-2 | |
| ATP Brisbane | 01/04 00:00 | 26 | Harrison, Ryan v Andy Murray | Cancelled | |
| ATP Brisbane | 01/01 01:00 | 25 | Harrison, Ryan v Mayer, Leonardo | 6-4,3-6,6-2 |