Stadium: Court 1 Round: 62 Ground: Clay
| ITF - Telfs M25 | 2021/07/13 09:10 | Taiyo Yamanaka v George Botezan | 1-6,1-6 |
| ITF - Telfs M25 | 2021/07/12 13:30 | Taiyo Yamanaka v Erwin Troebinger | 6-4,6-1 |
| ITF - Velenje M25 | 2021/07/06 08:00 | Alessandro Bellifemine v Taiyo Yamanaka | 6-3,6-2 |
| ITF - Velenje M25 | 2021/07/05 14:35 | Pietro R Scomparin v Taiyo Yamanaka | 2-6,6-1,7-10 |
| ITF - Wrocław M25 | 2021/06/28 09:40 | Taiyo Yamanaka v Petr Michnev | 5-7,2-6 |
| ITF - Wrocław M25 | 2021/06/27 12:30 | Juliusz Bienkiewicz v Taiyo Yamanaka | 3-6,1-6 |
| ITF - Skopje M15 | 2021/06/08 09:00 | Max Houkes v Taiyo Yamanaka | 6-4,6-3 |
| ITF - Skopje M15 | 2021/06/07 11:30 | Fons Van Sambeek v Taiyo Yamanaka | 6-2,2-6,6-10 |
| ITF - Sibenik M15 | 2021/05/17 15:40 | Leon Benedict v Mili Poljicak | 6-7,0-6 |
| ITF - Sibenik M15 | 2021/05/16 12:30 | Leon Benedict v Matthias Uwe Kask | 4-6,6-2,10-6 |
| ITF - Antalya M15 | 2021/04/18 07:00 | Daniel Siniakov v Leon Benedict | 6-2,6-1 |
| ITF - Antalya M15 | 2021/04/04 06:30 | Sandro Kopp v Leon Benedict | 6-2,6-4 |