High Five 2014 History
| Week # | Winners |
| 1 | No winners |
| 2 | No winners |
| 3 | Ka$h Money ($750) |
| 4 | No winners |
| 5 | UOENO & Gary B (split $500) |
| 6 | No winners |
| 7 | No winners |
| 8 | No winners |
| 9 | VictorVaz ($1000) |
| 10 | AT123 ($250) |
| 11 | No winners |
| 12 | No winners |
| 13 | No winners |
| 14 | No winners |
| 15 | Fraz ($1250) |
| 16 | No winners |
| 17 | Tiki ($500) |