Stadium: Center Round: 28 Ground: Hardcourt outdoor
| Honolulu, Simples W-ITF-USA-20A | 2019/07/12 20:00 | Kayla Day v Caroline Dolehide | 7-5,3-6,1-6 |
| Honolulu, Simples W-ITF-USA-20A | 2019/07/11 21:50 | Subhash, Natasha v Caroline Dolehide | 2-6,3-6 |
| Honolulu, Simples W-ITF-USA-20A | 2019/07/10 22:35 | Caroline Dolehide v Ayano Shimizu | 4-6,6-1,6-1 |
| Wimbledon Women | 2019/06/26 14:20 | Caroline Dolehide v Tereza Martincova | 1-6,6-7 |
| Wimbledon Women | 2019/06/25 10:30 | Cadantu, Alexandra v Caroline Dolehide | 1-6,6-3,3-6 |
| ITF W100 Ilkley | 2019/06/17 14:00 | Cepede Royg, Veronica v Caroline Dolehide | 6-3,6-4 |
| WTA Nottingham | 2019/06/09 12:20 | Caroline Dolehide v Cepede Royg, Veronica | 4-6,3-6 |
| ITF W100 Surbiton | 2019/06/06 12:25 | Alison Van Uytvanck v Caroline Dolehide | 6-4,3-6,6-4 |
| Honolulu, Simples W-ITF-USA-20A | 2019/07/12 22:00 | Gleason, Quinn v Gibbs, Nicole | 3-6,1-6 |
| Honolulu, Simples W-ITF-USA-20A | 2019/07/11 23:20 | Alycia Parks v Gibbs, Nicole | 2-6,2-6 |
| Honolulu, Simples W-ITF-USA-20A | 2019/07/11 00:00 | Whittle, Sophia v Gibbs, Nicole | 6-7,6-4,3-6 |
| ITF - W100 Bonita Springs | 2019/05/07 23:40 | Robin Anderson v Gibbs, Nicole | 2-6,6-4,6-1 |
| ITF W100 Charleston | 2019/05/03 18:45 | Gibbs, Nicole v Kaja Juvan | 1-6,4-6 |
| ITF W100 Charleston | 2019/05/02 17:00 | Gibbs, Nicole v Robin Anderson | 6-4,7-5 |
| ITF W100 Charleston | 2019/05/01 14:00 | Gibbs, Nicole v Karatantcheva, Sesil | 7-5,6-1 |
| Palm Harbor, Fl, Qualifications Simples W-ITF-USA-08A | 2019/04/07 16:00 | Gibbs, Nicole v Barbora Krejcikova | 0-6,1-6 |