The Winning Season Cast and Crew
 Sam Rockwell - (Bill) |
 Emma Roberts - (Abbie) |
 Margo Martindale - (Donna) |
 Rob Corddry - (Terry) |
 Jessica Hecht - (Stacey) |
| Shana Dowdeswell - (Molly) |
| Shareeka Epps - (Lisa) |
| Meaghan Witri - (Tamra) |
 Emily Rios - (Kathy) |
| Melanie Hinkle - (Mindy) |
 Rooney Mara - (Wendy) |
| Vanessa Gordillo - (Flor) |
 Connor Paolo - (Damon) |
| Melissa Graver - (New Rome Forward) |
| Clarke Thorell - (Prairie Hill Coach) |
| Rod Brogan - (Rick) |
| Kevin Breznahan - (Joel) |
| Brian Berrebbi - (Manager) |
| Rhonda Keyser - (Uno's Waitress) |
| Sara Chase - (Outback Waitress) |
| William Wiggins - (Teenager) |
| Colby Minifie - (Teen Girl) |
| Colleen Broomall - (New Rome Center) |
| Jennifer Regan - (Concerned Mother) |
| Devin Ratray - (Security Officer) |
| Ed Jewett - (Announcer) |
| Marceline Hugot - (Dr. Parsons) |
| E.J. Carroll - (Male Announcer) |
| Caitlin Colford - (Prairie Hill's Center) |
| Seth Herzog - (Mascot) |
| Lynn Mancinelli - (Cheerleader/Dancer #1) |
| Pauline Sherrow - (Cheerleader/Dancer #2) |
| Angelina Aucello - (Cheerleader/Dancer #3) |
| Robert Keir - (Arcade Boy) |
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