| ATP Montreal | 08/06 22:30 | 24 | [27] Nick Kyrgios v Kyle Edmund [33] | 3-6,4-6 | |
| ATP Washington | 08/02 18:00 | 27 | [122] Peter Gojowczyk v Kyle Edmund [34] | 6-3,4-6,6-3 | |
| ATP Washington | 08/01 18:00 | 26 | [34] Kyle Edmund v Jo-Wilfried Tsonga [70] | 4-6,6-3,6-4 | |
| ATP Washington | 07/30 20:40 | 25 | [34] Kyle Edmund v Lloyd Harris [85] | 6-1,6-4 | |
| Wimbledon | 07/03 13:15 | 24 | [30] Kyle Edmund v Fernando Verdasco [37] | 6-4,6-4,6-7,3-6,4-6 | |
| Wimbledon | 07/01 16:15 | 23 | [30] Kyle Edmund v Jaume Munar [90] | 6-4,6-4,6-4 | |
| ATP Eastbourne | 06/28 15:35 | 28 | [42] Taylor Fritz v Kyle Edmund [31] | 7-6,6-3 | |
| ATP Eastbourne | 06/27 15:45 | 27 | [31] Kyle Edmund v Daniel Evans [65] | 1-6,6-3,6-4 | |
| ATP Eastbourne | 06/26 15:50 | 26 | [31] Kyle Edmund v Cameron Norrie [49] | 6-2,6-2 | |
| ATP Queens | 06/19 17:35 | 25 | [6] Stefanos Tsitsipas v Kyle Edmund [30] | 6-3,7-5 | |
| French Open | 05/30 09:00 | 24 | [47] Pablo Cuevas v Kyle Edmund [30] | Retired | |
| French Open | 05/27 15:15 | 23 | [41] Jeremy Chardy v Kyle Edmund [30] | 6-7,7-5,4-6,6-4,5-7 | |
| ATP Rome | 05/13 09:00 | 24 | [38] Fernando Verdasco v Kyle Edmund [27] | 4-6,6-4,6-2 | |
| ATP Madrid | 05/07 12:00 | 24 | [12] Fabio Fognini v Kyle Edmund [22] | 6-4,6-3 | |
| ATP Munich | 04/30 14:10 | 25 | [22] Kyle Edmund v Denis Kudla [82] | 4-6,3-6 | |
| ATP Monte Carlo | 04/15 15:20 | 24 | [24] Diego Schwartzman v Kyle Edmund [23] | 4-6,6-3,6-1 | |
| ATP Marrakech | 04/10 15:45 | 26 | [22] Kyle Edmund v Jo-Wilfried Tsonga [116] | 6-7,3-6 | |
| ATP Marrakech | 04/08 14:10 | 25 | [22] Kyle Edmund v Ugo Humbert [63] | 6-3,6-2 | |
| ATP Miami | 03/26 16:00 | 26 | [22] Kyle Edmund v John Isner [9] | 6-7,6-7 | |
| ATP Miami | 03/24 17:55 | 25 | [14] Milos Raonic v Kyle Edmund [22] | 4-6,4-6 | |
| ATP Miami | 03/22 15:00 | 24 | [110] Ilya Ivashka v Kyle Edmund [22] | 3-6,2-6 | |
| ATP Indian Wells | 03/13 21:10 | 26 | [23] Kyle Edmund v Roger Federer [4] | 1-6,4-6 | |
| ATP Indian Wells | 03/12 23:25 | 25 | [53] Radu Albot v Kyle Edmund [23] | 3-6,3-6 | |
| ATP Indian Wells | 03/10 18:00 | 24 | [86] Nicolas Jarry v Kyle Edmund [23] | 2-6,0-6 | |
| Challenger Indian Wells | 03/03 20:30 | 29 | [27] Kyle Edmund v Andrey Rublev [112] | 6-3,6-2 | |
| Challenger Indian Wells | 03/02 21:50 | 28 | [27] Kyle Edmund v Lloyd Harris [99] | 6-2,4-6,6-1 | |
| Challenger Indian Wells | 03/01 21:30 | 27 | [27] Kyle Edmund v Yannick Maden [119] | 3-6,6-0,6-3 | |
| Challenger Indian Wells | 02/28 19:20 | 26 | [27] Kyle Edmund v Lukas Rosol [140] | 6-3,6-4 | |
| Challenger Indian Wells | 02/27 22:20 | 25 | [27] Kyle Edmund v Tommy Robredo [210] | 6-4,6-4 | |
| Australian Open | 01/14 05:35 | 23 | [14] Kyle Edmund v Tomas Berdych [57] | 3-6,0-6,5-7 |