| Week # | First Place | Second Place | Third Place | Fourth Place | Big Loser |
| 1 | Jaxieboy | 4leaf | Mattayb | Albino Rhino | Staniel |
| 2 | Big Red & Jai Kara | split with 1st | G Man | Bruteri | Moonlight |
| 3 | Raindrop2 | 5L | Jeep/Klizzle | split with 3rd | The Cheza |
| 4 | Primester | Brady Bunch | Sweet Merkins | Bruteri | Klizzle |
| 5 | Sol121 | Just Win Baby | Moonlight | Tulane84 | Gang Green |
| 6 | Rainboy | Biff54 |
Jai Kara/Abomb from Aroid |
split with 3rd | Raindrop2 |
| 7 | GoSunny | Raindrop1 | Jai Kara/ VictorVaz | split with 3rd | Phenom |
| 8 | 3com | Team America | 49ers & Tiki | split with 3rd | Lucky13JS |
| 9 | Motor City | Barney Boy | Kash Money | MyPriya | Raindrop2 |
| 10 | Bruteri | Kirti | Brady Bunch/ Rainboy | split with 3rd | ME2 |
| 11 | Brube/RTK | split with 1st | Barney Boy | Boogee Master/ Lil Smokey | Al the Greek |
| 12 | Primester | GMoney56 | Al the Greek/Jeep/ VictorVaz | split with 3rd | Art123 |
| 13 | Just Win Baby | Six Time Champs | Missbear | Lucky13JS | Snickers |
| 14 | Raindrop1 | Geechiedan | Lil Smokey | 4leaf/Barney Boy | Phenom |
| 15 | Gary B | Moonlight | Flyod's Fanatics | Tulane84 | G.O.A.T. |
| 16 | Jaxieboy | Sweet Merkins | Kirti | Iceman & MDJetsFan | Arvind |
| 17 | Beat My Boy | Six Time Champs | Missbear | Iceman | 1st Down Syndrome |
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) |
Primester's 2009 Prizes & Payouts
Weekly Pool Payouts - $800 per week paid out!
1st place = $400
2nd place = $200
3rd place = $125
4th place = $75
Halftime Payouts - $900 total to be paid out! (paid at end of week #8)
1st place = $ 500 = Just Win Baby
2nd place = $ 300 = Jai Kara
3rd place = $ 100 = Ateam & S&H (split)
Year-End Pool Payouts - $4000 total to be paid out!!
1st place = $1800 = Just Win Baby
2nd place = $1000 = Jai Kara
3rd place = $600 = JetsGirl
4th place = $320 = Biff54
5th & 6th place = $280 = Klizzle & Beat My Boy
Survivor I Pool Payout - 1st place = $ 3780 = EDMC, KCK, Klizzle, Pop, SOL121, Tulane84
Survivor 2 Pool Payout - 1st place = $1710 = Ateam, SOL121, SOL121-3
No Margin for Error Pool Payout - 1st place = $ 750 = Es Lo Que Hay
2nd place = $ 330 = Lucky 13JS
Beat my Boy - $200 = Bruteri, Raindrop2, SOL121, VictorVaz
Low Person Out - $200 = Rainboy
Big Loser of the Year - $250 = ME2