High Five 2021 History
| Week # | Winners |
| 1 | No winners |
| 2 | No winners |
| 3 | Quedezzy & GCasanova |
| 4 | JimCron |
| 5 | No winners |
| 6 | Kash Money |
| 7 | GCasanova & Primester |
| 8 | No winners |
| 9 | No winners |
| 10 | Thread the Needle |
| 11 | No winners |
| 12 | Es Lo Que Hay |
| 13 | Fulchino & Pixote |
| 14 | Ghost Nappa |
| 15 | Kash Money |
| 16 | Lil Smokey, RJS10 & Trackster |
| 17 | RJS10 |
| 18 | azehC ehT & Brube |