Stadium: Court 12 Round: 44 Ground: Clay
| Ashland, Simples W-ITF-USA-23A | 2019/07/22 13:00 | Shaffer, Kennedy v Small, Rosalyn | 6-0,6-0 |
| ITF Women Sumter | 2017/10/07 13:00 | Shaffer, Kennedy v Small, Rosalyn | 6-0,6-0 |
| ITF W60 Charleston | 2019/09/30 17:30 | Panna Udvardy v Shaffer, Kennedy | 6-3,6-1 |
| ITF W60 Lexington | 2019/07/30 16:45 | Shaffer, Kennedy v Peyton Stearns | 5-7,4-6 |
| Ashland, Simples W-ITF-USA-23A | 2019/07/23 13:00 | Shaffer, Kennedy v Glatch, Alexa | 3-6,0-6 |
| Ashland, Simples W-ITF-USA-23A | 2019/07/22 13:00 | Shaffer, Kennedy v Small, Rosalyn | 6-0,6-0 |
| ITF W25 Saskatoon | 2019/07/08 21:10 | Shaffer, Kennedy v Livianu, Jessica | 1-6,2-6 |
| ITF W25 Sumter | 2019/06/11 17:45 | Montez, Pamela v Shaffer, Kennedy | 6-2,6-1 |
| ITF W25 Pelham | 2019/04/10 15:00 | Dasha Ivanova v Shaffer, Kennedy | 6-3,6-1 |
| WTA - Charleston | 2019/03/30 17:25 | Conny Perrin v Shaffer, Kennedy | 6-0,6-1 |
| New Haven, USA | 2019/09/04 19:15 | Cepelova, Jana v Small, Rosalyn | 6-0,6-0 |
| Landisville, Qualifications Simples W-ITF-USA-29A | 2019/08/05 15:10 | Xiaodi You v Small, Rosalyn | 6-0,6-0 |
| Ashland, Simples W-ITF-USA-23A | 2019/07/22 13:00 | Shaffer, Kennedy v Small, Rosalyn | 6-0,6-0 |
| Shreveport, Singles Qualifying W-ITF-USA-19A | 2019/06/24 15:30 | Small, Rosalyn v Clousing, Keisha R | 0-6,1-6 |
| ITF W15 Naples | 2019/05/13 14:30 | Payton Andrews v Small, Rosalyn | 6-0,6-0 |
| ITF W100 Charleston | 2019/04/29 18:45 | Small, Rosalyn v Woolcock, Belinda | 0-6,0-6 |
| Charlottesville, Simples W-ITF-USA-13A | 2019/04/22 15:15 | Rasheeda McAdoo v Small, Rosalyn | 6-0,6-0 |
| Palm Harbor, Fl, Qualifications Simples W-ITF-USA-08A | 2019/04/01 14:00 | Akgul Amanmuradova v Small, Rosalyn | 6-0,6-0 |