Stadium: Cancha 3 Round: 26 Ground: Clay
| ITF W25 Guayaquil | 2019/08/13 20:20 | Chieh-Yu Hsu v Jasmin Jebawy | 6-1,6-2 |
| ITF W25 Fort Worth | 2019/08/01 14:00 | Whittle, Sophia v Chieh-Yu Hsu | 0-6,6-2,6-1 |
| ITF W25 Fort Worth | 2019/07/31 14:55 | Rhiann Newborn v Chieh-Yu Hsu | 1-6,2-6 |
| ITF W25 Evansville | 2019/07/24 14:00 | Fahey, Katharine v Chieh-Yu Hsu | 4-6,7-5,7-5 |
| Gatineau, Singles W-ITF-CAN-04A | 2019/07/18 15:30 | Susan Bandecchi v Chieh-Yu Hsu | 6-2,6-7,6-2 |
| Gatineau, Singles W-ITF-CAN-04A | 2019/07/16 16:35 | Nagi Hanatani v Chieh-Yu Hsu | 3-6,1-6 |
| ITF W25 Saskatoon | 2019/07/10 19:05 | Chieh-Yu Hsu v Maddison Inglis | 3-6,2-6 |
| Shreveport, Singles Qualifying W-ITF-USA-19A | 2019/06/30 15:30 | Alycia Parks v Chieh-Yu Hsu | 2-6,3-6 |
| ITF W25 Guayaquil | 2019/08/13 17:00 | Stewart, Katerina v Kurata, Nathaly | 6-2,6-2 |
| Bethany Beach, Singles W-ITF-USA-17A | 2019/06/07 15:55 | Tess Sugnaux v Stewart, Katerina | 6-2,7-6 |
| Bethany Beach, Singles W-ITF-USA-17A | 2019/06/06 16:05 | Fahey, Katharine v Stewart, Katerina | 6-3,3-6,3-6 |
| ITF W15 Naples | 2019/05/19 14:30 | Woolcock, Belinda v Stewart, Katerina | 4-6,3-6 |
| ITF W15 Naples | 2019/05/18 14:30 | Peyton Stearns v Stewart, Katerina | 2-6,6-7 |
| ITF W15 Naples | 2019/05/17 17:05 | Hance, Kimmi v Stewart, Katerina | 0-6,1-6 |
| ITF W15 Naples | 2019/05/16 19:30 | Eleana Yu v Stewart, Katerina | 2-6,2-6 |
| ITF W15 Naples | 2019/05/14 14:00 | Kobelt, Madeleine v Stewart, Katerina | 2-6,3-6 |