| WTA Charleston | 04/01 16:50 | 24 | [126] Caroline Wozniacki v McCartney Kessler [122] | 6-0,6-1 | |
| WTA Charleston | 03/31 18:20 | 19 | [120] McCartney Kessler v Sachia Vickery [131] | 6-7,3-6 | |
| WTA Charleston | 03/30 16:25 | 14 | [120] McCartney Kessler v Haley Giavara [433] | 6-2,6-1 | |
| WTA San Luis Potosi | 03/26 16:00 | 25 | [120] McCartney Kessler v Nadia Podoroska [78] | 6-7,6-4,3-6 | |
| WTA Miami | 03/17 15:00 | 14 | [123] McCartney Kessler v Camila Osorio [91] | 3-6,6-1,2-6 | |
| WTA Charleston | 03/14 16:10 | 27 | [123] McCartney Kessler v Elisabetta Cocciaretto [60] | 5-7,3-6 | |
| WTA Charleston | 03/13 15:25 | 26 | [123] McCartney Kessler v Kamilla Rakhimova [95] | 7-5,6-2 | |
| WTA Charleston | 03/12 14:00 | 25 | [62] Lin Zhu v McCartney Kessler [123] | 6-3,4-6,5-7 | |
| WTA Charleston | 03/11 16:40 | 19 | [120] Mai Hontama v McCartney Kessler [123] | 1-6,2-6 | |
| WTA Charleston | 03/10 18:55 | 14 | [110] Darja Semenistaja v McCartney Kessler [123] | 3-6,1-6 | |
| WTA Indian Wells | 03/07 20:55 | 23 | [123] McCartney Kessler v Nuria Parrizas-Diaz [134] | 3-6,6-7 | |
| WTA Puerto Vallarta | 02/26 00:00 | 29 | [192] Taylah Preston v McCartney Kessler [153] | 7-5,3-6,0-6 | |
| WTA Puerto Vallarta | 02/25 01:35 | 28 | [114] Hailey Baptiste v McCartney Kessler [153] | 4-6,4-6 | |
| WTA Puerto Vallarta | 02/23 22:20 | 27 | [153] McCartney Kessler v Leolia Jeanjean [147] | 6-2,6-1 | |
| WTA Puerto Vallarta | 02/22 20:00 | 26 | [109] Claire Liu v McCartney Kessler [153] | 4-6,3-6 | |
| WTA Puerto Vallarta | 02/21 01:45 | 25 | [153] McCartney Kessler v Natalija Stevanovic [187] | 6-3,6-1 | |
| WTA Puerto Vallarta | 02/19 17:00 | 14 | [153] McCartney Kessler v Liv Hovde [296] | 4-6,6-4,1-6 | |
| ITF W75 Rome (GA) | 02/04 16:55 | 29 | [317] Liv Hovde v McCartney Kessler [177] | 4-6,1-6 | |
| ITF W75 Rome (GA) | 02/03 18:20 | 28 | [177] McCartney Kessler v Hailey Baptiste [121] | 2-6,6-3,6-3 | |
| ITF W75 Rome (GA) | 02/02 18:05 | 27 | [177] McCartney Kessler v Robin Montgomery [198] | 7-6,6-3 | |
| ITF W75 Rome (GA) | 02/01 16:00 | 26 | [177] McCartney Kessler v Veronika Miroshnichenko [320] | 6-1,6-3 | |
| ITF W75 Rome (GA) | 01/30 19:05 | 25 | [177] McCartney Kessler v Grace Min [286] | 6-4,6-1 | |
| Australian Open Women | 01/18 00:00 | 24 | [206] McCartney Kessler v Linda Noskova [50] | 3-6,6-1,4-6 | |
| Australian Open Women | 01/15 03:15 | 23 | [153] Fiona Ferro v McCartney Kessler [206] | 6-3,3-6,2-6 | |
| WTA Auckland | 01/01 23:00 | 25 | [217] McCartney Kessler v Lulu Sun [214] | 4-6,3-6 | |
| WTA Auckland | 12/30 22:00 | 19 | [221] McCartney Kessler v Ya Yi Yang [210] | 7-5,6-4 | |
| WTA Auckland | 12/29 23:55 | 45 | [133] Jessika Ponchet v McCartney Kessler [221] | 2-6,7-6,3-6 | |
| WTA Limoges | 12/14 17:35 | 26 | [224] McCartney Kessler v Erika Andreeva [120] | 6-4,5-7,2-6 | |
| WTA Limoges | 12/11 12:45 | 25 | [224] McCartney Kessler v Margaux Rouvroy [232] | 4-6,6-1,6-0 | |
| WTA Angers | 12/08 11:40 | 27 | [106] Dayana Yastremska v McCartney Kessler [235] | 5-7,6-3,7-6 |