| WTA Angers | 12/08 11:40 | 27 | [106] Dayana Yastremska v McCartney Kessler [235] | 5-7,6-3,7-6 | |
| WTA Angers | 12/06 13:50 | 26 | [330] Francesca Curmi v McCartney Kessler [235] | 4-6,3-6 | |
| WTA Angers | 12/04 09:00 | 25 | [235] McCartney Kessler v Clara Tauson [82] | 7-6,6-3 | |
| ITF W100 Charleston | 11/09 15:00 | 26 | [231] McCartney Kessler v Panna Udvardy [140] | 5-7,4-6 | |
| ITF W100 Charleston | 11/08 14:50 | 25 | [223] Nigina Abduraimova v McCartney Kessler [231] | 7-6,6-7,5-7 | |
| WTA Midland | 11/01 17:15 | 25 | [237] McCartney Kessler v Emina Bektas [104] | 6-2,4-6,5-7 | |
| ITF W80 Tyler | 10/27 00:00 | 26 | Ayana Akli v McCartney Kessler | 7-5,6-3 | |
| ITF W80 Tyler | 10/24 20:00 | 25 | Ellie Douglas v McCartney Kessler | 6-4,1-6,3-6 | |
| ITF W80 Macon | 10/19 17:50 | 26 | [80] Taylor Townsend v McCartney Kessler [244] | 6-1,6-4 | |
| ITF W80 Macon | 10/17 18:05 | 25 | [244] McCartney Kessler v Catherine Harrison [247] | 6-1,7-5 | |
| ITF W60 Rome, GA | 10/08 14:55 | 29 | [288] McCartney Kessler v Grace Min [304] | 6-2,6-1 | |
| ITF W60 Rome, GA | 10/07 16:20 | 28 | [288] McCartney Kessler v Renata Zarazua [169] | 6-4,6-4 | |
| ITF W60 Rome, GA | 10/06 14:00 | 27 | [288] McCartney Kessler v Anastasia Tikhonova [236] | 6-7,6-3,7-6 | |
| ITF W60 Rome, GA | 10/05 15:45 | 26 | [288] McCartney Kessler v Sahaja Yamalapalli [413] | 6-4,6-2 | |
| ITF W60 Rome, GA | 10/04 16:05 | 25 | [77] Taylor Townsend v McCartney Kessler [288] | 2-6,4-6 | |
| ITF W60 Templeton | 09/30 20:00 | 28 | [89] Taylor Townsend v McCartney Kessler [310] | 7-5,6-4 | |
| ITF W60 Templeton | 09/29 18:55 | 27 | [338] Hanna Chang v McCartney Kessler [310] | 5-7,2-6 | |
| ITF W60 Templeton | 09/28 21:05 | 26 | [310] McCartney Kessler v Hailey Baptiste [137] | 3-6,6-3,6-1 | |
| ITF W60 Templeton | 09/27 22:00 | 25 | [231] Carmen Corley v McCartney Kessler [310] | 3-6,2-6 | |
| ITF W60 Berkeley | 09/21 17:00 | 26 | [209] Tatiana Prozorova v McCartney Kessler [310] | 6-2,7-6 | |
| ITF W60 Berkeley | 09/20 18:50 | 25 | McCartney Kessler v Alexa Noel | 7-6,6-2 | |
| US Open femminili | 08/26 19:30 | 19 | [363] McCartney Kessler v Eva Lys [145] | 2-6,1-6 | |
| US Open femminili | 08/25 20:30 | 15 | [363] McCartney Kessler v Su Jeong Jang [152] | 6-2,6-4 | |
| US Open femminili | 08/23 21:00 | 14 | [102] Yue Yuan v McCartney Kessler [363] | 6-4,2-6,6-7 | |
| ITF W100 Landisville | 08/10 21:40 | 26 | [71] Xinyu Wang v McCartney Kessler [378] | 6-4,6-4 | |
| ITF W100 Landisville | 08/09 15:00 | 25 | [378] McCartney Kessler v Himeno Sakatsume [197] | 3-6,6-4,6-2 | |
| ITF W60 Lexington | 08/04 17:40 | 27 | [148] Olivia Gadecki v McCartney Kessler [411] | 7-5,7-6 | |
| ITF W60 Lexington | 08/03 23:10 | 26 | [411] McCartney Kessler v Katie Volynets [125] | 6-0,6-3 | |
| ITF W60 Lexington | 08/01 17:40 | 25 | [320] Whitney Osuigwe v McCartney Kessler [411] | 6-0,4-6,3-6 | |
| ITF W60 Dallas | 07/27 17:25 | 26 | [435] McCartney Kessler v Yafan Wang [182] | 2-6,4-6 |