The second installment of the Gamble Cup was played in October, 2009 due to scheduling conflicts. This cloudy and cool day at Puslinch Golf and Country Club brought tough competition for the defending champion by main challengers
Gary Gamble and Kyle Frasier who each admittedly stepped up their game in the final month of the season to make a run at the championship. Frasier was basically eliminated after a partial meltdown on the par 3 17th hole setting up a showdown between Gary Gamble and Stephen Gamble.
On the par 4 18th, eldest brother Gary Gamble charged from a one point deficit and tied the match forcing a sudden death playoff hole. Replaying the 18th with the eliminated players watching from the green, a clutch put on the 18th short grass sealed a second consecutive victory for Stephen Gamble who retained possession of the cup.