| ITF W35 Nottingham | 05/02 09:00 | 26 | Madison Sieg v Hikaru Sato | 6-7,6-4,1-6 | |
| ITF W35 Nottingham | 04/30 12:35 | 25 | Madison Sieg v Jaquelyn Ogunwale | 6-2,6-0 | |
| ITF W35 Nottingham | 04/25 09:00 | 26 | Johanne C Svendsen v Madison Sieg | 6-3,1-6,6-2 | |
| ITF W35 Nottingham | 04/23 09:00 | 25 | Elena-Teodora Cadar v Madison Sieg | 6-7,5-7 | |
| ITF W75 Florianópolis | 04/03 14:55 | 26 | Madison Sieg v Solana Sierra | 1-6,3-6 | |
| ITF W75 Florianópolis | 04/03 14:30 | - | [337] Madison Sieg v Solana Sierra [179] | 1-6,3-6 | |
| ITF W75 Florianópolis | 04/01 14:30 | 25 | [299] Ana Candiotto v Madison Sieg [337] | 1-6,3-6 | |
| ITF W50 São Paulo | 03/28 01:00 | 25 | [333] Carolina Alves v Madison Sieg [337] | 6-3,6-2 | |
| WTA Charleston | 03/12 14:00 | 25 | [343] Madison Sieg v Oceane Dodin [85] | 3-6,2-6 | |
| ITF W35 Santo Domingo | 03/06 13:40 | 25 | [476] Nahia Berecoechea v Madison Sieg [343] | 6-1,6-4 | |
| WTA San Diego | 02/24 19:25 | 14 | [89] Kayla Day v Madison Sieg [332] | 6-3,6-3 | |
| ITF W35 Wesley Chapel | 02/10 15:00 | 28 | [341] Madison Sieg v Leonie Kung [377] | 3-6,3-6 | |
| ITF W35 Wesley Chapel | 02/09 17:05 | 27 | Lea Ma v Madison Sieg | Retired | |
| ITF W35 Wesley Chapel | 02/08 14:00 | 26 | [429] Marine Partaud v Madison Sieg [341] | 6-7,0-6 | |
| ITF W35 Wesley Chapel | 02/07 16:25 | 25 | Ava Markham v Madison Sieg | 2-6,3-6 | |
| ITF W75 Rome (GA) | 02/01 15:50 | 26 | [352] Madison Sieg v Stacey Fung [237] | 3-6,6-7 | |
| ITF W75 Rome (GA) | 01/31 15:00 | 25 | [315] Gabriela Lee v Madison Sieg [352] | 6-3,4-6,4-6 | |
| ITF W75 Vero Beach | 01/24 00:10 | 25 | [353] Madison Sieg v Maria Lourdes Carle [124] | 6-4,1-6,1-6 | |
| ITF W35 Naples | 01/19 19:00 | 27 | [262] Marie Benoit v Madison Sieg [353] | 6-1,6-4 | |
| ITF W35 Naples | 01/18 17:20 | 26 | [353] Madison Sieg v Hanna Chang [251] | 7-6,4-6,7-5 | |
| ITF W35 Naples | 01/17 15:00 | 25 | Lea Ma v Madison Sieg | 4-6,4-6 | |
| ITF W35 Naples | 01/09 19:25 | 25 | [492] Clervie Ngounoue v Madison Sieg [350] | 6-1,6-2 | |
| ITF W25 Austin | 11/18 16:55 | 28 | [369] Madison Sieg v Hanna Chang [320] | 6-7,2-6 | |
| ITF W25 Austin | 11/17 16:55 | 27 | [369] Madison Sieg v Catherine Harrison [362] | 7-5,6-3 | |
| ITF W25 Austin | 11/16 17:50 | 26 | [315] Ava Markham v Madison Sieg [369] | 4-6,2-6 | |
| ITF W25 Austin | 11/14 19:50 | 25 | [479] Maria Kozyreva v Madison Sieg [369] | 2-6,0-6 | |
| ITF W60 Calgary | 11/09 17:50 | 26 | [383] Madison Sieg v Arina Rodionova [148] | 3-6,1-6 | |
| 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 |