Joe Daley, 2005
Daley outdueled fishing and hunting buddy Shane Bertsch in a one-hole playoff at Crestview for his second Web.com Tour victory. At the time, Daley, who didn’t turn professional until age 32, became the tournament’s oldest champion at 44. After two seasons on the PGA Tour and a decade on the developmental tour, Daley’s biggest career victory came after 50 at the 2012 Senior Players Championship. It was just months after he earned Champions Tour status by tying for fourth in the Senior PGA Championship. Daley has earned more than $1 million on both Web.com and Champions tours.