When does Win or Lose return?

Win or Lose premiered on Disney+ on February 19, 2025, and consisted of eight episodes releasing weekly in groups of two until March 12. Each episode focuses on a central character - either a member of the Pickles or one of their loved ones or acquaintances - whose life begins falling apart during the given week. The series' cast includes Will Forte, Ian Chen, Izaac Wang, Jo Firestone, Milan Ray, Josh Thomson, Erin Keif, Rosie Foss, Chanel Stewart, Dorien Watson, Lil Rel Howery, Flula Borg, Kyliegh Curran, Jaylin Fletcher, Tom Law, Beck Nolan, Orion Tran.