| ITF W60 Calgary | 11/08 20:55 | 25 | [383] Madison Sieg v Kayla Cross [274] | 3-6,6-4,6-4 | |
| ITF W60 Toronto | 10/26 19:00 | 26 | [198] Jana Fett v Madison Sieg [359] | 6-0,6-2 | |
| ITF W60 Toronto | 10/24 14:00 | 25 | Madison Sieg v Anna Ulyashchenko | 6-1,1-6,6-0 | |
| ITF W60 Saguenay | 10/20 19:05 | 27 | Madison Sieg v Isabelle Boulais | 3-6,6-7 | |
| ITF W60 Saguenay | 10/19 15:55 | 26 | [487] Dalayna Hewitt v Madison Sieg [388] | 3-6,3-6 | |
| ITF W60 Saguenay | 10/18 19:45 | 25 | [388] Madison Sieg v Jasmin Jebawy [399] | 6-2,6-2 | |
| ITF W60 Rancho Santa Fe | 10/10 21:10 | 25 | [227] Stacey Fung v Madison Sieg [381] | 6-3,6-4 | |
| ITF W25 Santarem | 09/26 08:30 | 54 | Madison Sieg v Danielle Willson | 3-6,2-6 | |
| ITF W25 Santarem | 09/25 10:40 | 54 | Madison Sieg v Dana Daniela Avramenko | 6-0,6-0 | |
| ITF W25 Ceuta | 09/21 09:35 | 26 | Clara Vlasselaer v Madison Sieg | 7-6,6-2 | |
| ITF W25 Ceuta | 09/20 11:10 | 25 | [466] Jacqueline Cabaj Awad v Madison Sieg [420] | 6-4,1-6,1-6 | |
| ITF W25 Leiria | 09/16 13:00 | 28 | [219] Anastasia Zakharova v Madison Sieg [422] | 4-6,6-2,6-0 | |
| ITF W25 Leiria | 09/15 10:00 | 27 | [434] Eva Guerrero Alvarez v Madison Sieg [422] | 4-6,2-6 | |
| ITF W25 Leiria | 09/14 14:40 | 26 | Madison Sieg v Gyeong Seo Lee | 0-6,6-4,6-2 | |
| ITF W25 Leiria | 09/12 10:00 | 25 | [403] Kathleen Kanev v Madison Sieg [422] | 3-6,1-6 | |
| WTA Stanford | 08/12 21:00 | 14 | [441] Madison Sieg v Valeria Savinykh [178] | 3-6,2-6 | |
| ITF W100 Landisville | 08/10 22:05 | 26 | Mary Stoiana v Madison Sieg | 7-5,6-3 | |
| ITF W100 Landisville | 08/09 15:00 | 25 | [316] Sophie Chang v Madison Sieg [441] | 6-3,6-7,2-6 | |
| ITF W100 Landisville | 08/08 15:40 | 54 | [322] Whitney Osuigwe v Madison Sieg [441] | 3-6,5-7 | |
| ITF W60 Lexington | 08/01 17:05 | 25 | [148] Olivia Gadecki v Madison Sieg [440] | 7-5,6-3 | |
| ITF W60 Dallas | 07/26 16:40 | 25 | [103] Madison Brengle v Madison Sieg [395] | 6-4,6-1 | |
| ITF W60 Dallas | 07/25 18:05 | 54 | Madison Sieg v Ganna Poz'renko | 6-0,6-3 | |
| ITF W60 Dallas | 07/24 21:10 | 54 | Madison Sieg v Nicole Khirin | 6-3,6-3 | |
| ITF W60 Evansville | 07/19 18:20 | 25 | Madison Sieg v Allie Kiick | 1-6,1-6 | |
| ITF W40 L'Aia | 07/05 16:45 | 25 | Madison Sieg v Michaela Laki | 3-6,6-0,3-6 | |
| ITF W40 L'Aia | 07/03 10:00 | 54 | Madison Sieg v Merel Hoedt | 6-1,2-6,6-4 | |
| ITF W40 L'Aia | 07/02 08:00 | 54 | Madison Sieg v Emilie Elde | 6-0,6-4 | |
| ITF W25 Perigueux | 06/28 13:00 | 25 | [270] Margaux Rouvroy v Madison Sieg [382] | 7-5,7-5 | |
| ITF W25 Guimaraes | 06/18 09:55 | 29 | Madison Sieg v Gabriela Knutson | 3-6,4-6 | |
| ITF W25 Guimaraes | 06/17 11:50 | 28 | Madison Sieg v Katy Dunne | 5-7,6-2,6-3 |