Guest Stars Michael Reilly Burke as Coach Flynn Chad L. Coleman as Ray Perkins Joel Swetow as Chiropractor Brandon Mychal Smith as Billy York Christopher Stapleton as Wayne Wilmers Jarrod Bunch as Coach Tom Bryant Co Starring Kelsey Crane as Female Bartender Blair Hickey as Ken Newman Aedin Mincks as Walter, Jr. James Wellington as Logan Clark Dustin Cyril Robles as Finnegan Ian Gregory as Coach Simms Mike Mauloff as Ralph the Trivia Guy Oren Skoog as Jason Latimer James Giordano as Superintendent Natalia Castellanos as Waitress