2011 Week 5 Skills Challenge Champion: Josh Isler
- Champion: Josh Isler
- Group: Christ Community Church
- Venue: Applecross Country Club
In Week 5, Winning Golf traveled to a new and beautiful course in Chester County, Applecross C.C. Host Paul Clough brought out 11 enthusiastic golfers and after 5 rounds of friendly competition, Josh Isler defeated Tom Corcimgilia in the finals.