High Five 2009 History
| Week # | Winners |
| 1 | No Winners |
| 2 | Jai Kara & KCK (split $400) |
| 3 | GNO |
| 4 | SOL121 |
| 5 | No Winners |
| 6 | No Winners |
| 7 | Albino Rhino, GNO, Iceman, Jai Kara, MDJetsFan, ObamaSucks (split $600) |
| 8 | No Winners |
| 9 | No Winners |
| 10 | No Winners |
| 11 | BRube ($800) |
| 12 | No Winners |
| 13 | No Winners |
| 14 | No Winners |
| 15 | No Winners |
| 16 | No Winners |
| 17 | BRube, Jai Kara, KCK, MDJetsFan, Primester, SOL121 (split $1200) |