2014 Winner's (& Loser's) Circle
| Week # | First Place | Second Place | Third Place | Fourth Place | Big Loser |
| 1 | Lucky13JS | Mad Men | Hodor | Glassgirl | Cia Pet |
| 2 | Trackster | River Rat | Klizzle | GMoney56 | DGear |
| 3 | Big Red & Sikdiddy | see 1st place | Arvind | GABahn911 & Motor City | Trackster |
| 4 | Packman | Brube | Kash Money | VictorVaz | River Rat |
| 5 | Big Red | Hodor | Iceman | Trackster | Arvind |
| 6 | Klizzle | Ateam | Tuffy | 4leaf & Jon Jon | Brube |
| 7 | Biff54 | Ateam | Mickey Slick | Full Commission & Lucky13JS | Lil Smokey |
| 8 | KCK | Mickey Slick | Al the Greek, Cia Pet & Primester | see 3rd place | Ballslapper |
| 9 | Lucky13js | Turf Toe | Joeey | 3com & Messier | VodkaBall |
| 10 | Gman14 | 5L & Shiloh | see 2nd place | Motor City | Lil Smokey |
| 11 | Mad Men | Lil Smokey | Biff 54 | Mickey Slick | Sol121 |
| 12 | Trackster | Richie Rich | Glassgirl | GMan14 | VodkaBall |
| 13 | Arvind | Klizzle | River Rat | Ballslapper | Gmoney56 |
| 14 | Trackster | GMoney56 | 3com | Biff54 | Glassgirl |
| 15 | GMoney56 | SikDiddy | 3com | Fretster | Cia Pet |
| 16 | 5L | Biff54 | UOENO | Gman14 | 4leaf |
| 17 | Highway Man | Fretster | Al the Greek & GABahn911 | see 3rd place | Jon Jon |
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) |
Weekly Pool Payouts - $ per week paid out!
1st place = $350
2nd place = $200
3rd place = $100
4th place = $50
Halftime Payouts - $900 total to be paid out! (paid at end of week #8)
1st/2nd place = $800 = Motor City & Packman
3rd place = $100 = Big Red, Hodor & Beat My Boy
Year-End Pool Payouts - $2500 total to be paid out!!
1st/2nd place = $1750 = Trackster & Biff54
3rd/4th place = $625 = River Rat & Big Red
5th place = $125 = Hodor, Motor City, Ateam & Packman
High Five Pool Payout - $250 per week
"Draft" Pool Payout -1st place = $770 = Primester
2nd place = $330 = Brube
Survivor I Pool Payout - 1st place = $2800 = Fretster
2nd place = $1190 = Gwapville
Survivor II Pool Payout - 1st/2nd place = $2430 = Beast Mode, GCasanova, Hammerhead
No Margin for Error Pool Payout - 1st place = $485 = Brube
2nd place = $205 = Larry Trillips
Beat my Boy - $200 = Motor City
Low Person Out - $200 = 3com
Big Loser of the Year - $250 = Barney Boy