We're guessing The Winning Season was, most likely, a script that writer-director James C. Strouse (Grace is Gone) wanted to sell to a studio like Disney but couldn't, so, instead, he decided to suck it up, shoot on DV Cam, try to get the most name brand talent he could (in this case, Emma Roberts and Sam Rockwell) and shoot his vision.
Sam Rockwell stars as a former high school basketball star who's now a divorced, alcoholic dish washer relegated to stealing leftover food and drinks from the tables he buses.