Cast of Win Win
24 credited, in billing order.
Paul Giamattias Mike Flaherty
Amy Ryanas Jackie Flaherty
Bobby Cannavaleas Terry Delfino
Jeffrey Tamboras Vigman
Burt Youngas Leo Poplar
Melanie Lynskeyas Cindy Timmons
Alex Shafferas Kyle
Margo Martindaleas Eleanor
David Thompsonas Stemler
Nina Ariandaas Shelly
Mike Diliello
Mike Dilielloas Jimmy Reed
Marcia Haufrechtas Gina Flaherty
Sharon Wilkinsas Judge Lee
Clare Foleyas Abby
Penelope Kindredas Stella
Sophie Kindredas Stella
Tim Ransomas Stuart Thatcher
Nicholas Somers
Nicholas Somersas BHS Coach
Jacqueline Brogan
Jacqueline Broganas Woman Jogging
Marceline Hugotas Woman Jogging
Edmund Ikedaas Frank
Joseph Tibonias Steve Deluca / Principal
Pam Levineas Church Soloist
Darren Goldsteinas Sheffield Coach
