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