| US Open Women | 08/24 19:35 | 14 | [222] Yuki Naito v Ahn, Kristie [140] | 6-4,3-6,6-3 | |
| WTA Cincinnati | 08/14 20:20 | 14 | Ahn, Kristie v Lauren Davis | 6-4,2-6,2-6 | |
| WTA Montreal | 08/08 16:00 | 19 | [68] Caroline Garcia v Ahn, Kristie [138] | 7-6,6-3 | |
| WTA Montreal | 08/07 16:10 | 14 | [12] Melichar, Nicole v Ahn, Kristie [138] | 6-1,5-7,0-6 | |
| WTA San Jose | 07/31 18:35 | 14 | [116] Ahn, Kristie v Na-Lae Han [266] | 3-6,6-2,0-6 | |
| Wimbledon Women | 06/30 18:15 | 24 | [117] Ahn, Kristie v Sloane Stephens [73] | 5-7,3-6 | |
| Wimbledon Women | 06/28 18:05 | 23 | [117] Ahn, Kristie v Heather Watson [68] | 2-6,7-6,8-6 | |
| Wimbledon Women | 06/25 10:30 | 19 | [118] Ahn, Kristie v Niculescu, Monica [193] | 5-7,1-6 | |
| Wimbledon Women | 06/24 10:00 | 15 | [118] Ahn, Kristie v Ekaterine Gorgodze [209] | 6-2,6-3 | |
| Wimbledon Women | 06/22 18:10 | 14 | [118] Ahn, Kristie v Caroline Dolehide [163] | 1-6,7-5,6-2 | |
| ITF W100 Nottingham | 06/16 11:35 | 25 | [119] Ahn, Kristie v Katarzyna Kawa [134] | 4-6,4-6 | |
| WTA Nottingham | 06/08 13:30 | 25 | [72] Viktorija Golubic v Ahn, Kristie [123] | Retired | |
| WTA Nottingham | 06/06 13:30 | 24 | [123] Ahn, Kristie v Burrage, Jodie Anna [250] | 1-6,6-3,6-2 | |
| French Open Women | 05/25 14:10 | 14 | [123] Ahn, Kristie v Vandeweghe, Coco [223] | 6-3,3-6,4-6 | |
| ITF W100 Bonita Springs | 05/12 21:25 | 25 | [310] Irina Fetecau v Ahn, Kristie [121] | 6-3,7-5 | |
| ITF W100 Charleston | 05/04 17:30 | 25 | [124] Ahn, Kristie v Magdalena Frech [158] | 4-6,3-6 | |
| ITF W60 Charlottesville | 04/28 18:15 | 25 | [432] Maria Mateas v Ahn, Kristie [124] | 3-6,6-4,6-3 | |
| WTA - Charleston | 04/13 17:00 | 25 | [122] Ahn, Kristie v Di Lorenzo, Francesca [151] | 6-7,2-6 | |
| WTA - Bogota | 04/05 15:00 | 25 | [119] Ahn, Kristie v Jasmine Paolini [103] | 3-6,0-6 | |
| WTA - Miami | 03/23 15:50 | 19 | [160] Olga Danilovic v Ahn, Kristie [121] | 7-6,6-3 | |
| WTA - Miami | 03/22 17:45 | 14 | [151] Di Lorenzo, Francesca v Ahn, Kristie [121] | 1-6,4-6 | |
| WTA Monterrey | 03/13 16:00 | 14 | [114] Ahn, Kristie v Usue Maitane Arconada [156] | 4-6,6-7 | |
| ITF W100 Charleston | 11/04 18:40 | 25 | [149] Caroline Dolehide v Ahn, Kristie [107] | 6-1,6-0 | |
| ITF W80 Tyler | 10/29 16:55 | 25 | [245] Hailey Baptiste v Ahn, Kristie [106] | 6-2,6-2 | |
| ITF W80 Macon | 10/22 16:20 | 26 | [137] Sara Errani v Ahn, Kristie [105] | 6-3,6-4 | |
| ITF W80 Macon | 10/21 22:05 | 25 | [253] Tessah Andrianjafitrimo v Ahn, Kristie [105] | 3-6,3-6 | |
| French Open Women | 09/28 13:05 | 23 | [102] Ahn, Kristie v Williams, Serena [9] | 6-7,0-6 | |
| US Open Women | 09/01 21:05 | 23 | [96] Ahn, Kristie v Williams, Serena [8] | 5-7,3-6 | |
| New York, USA | 08/21 16:50 | 19 | [111] Leylah Fernandez v Ahn, Kristie [97] | 6-4,6-1 | |
| New York, USA | 08/20 17:25 | 44 | [108] Anna-Lena Friedsam v Ahn, Kristie [97] | 5-7,0-6 |