TV Dark Side of Football - Season 1 Episode 5 : Why Can't Cleveland Win? Dark Side of Football - Season 1 Episode 5 : Why Can't Cleveland Win? 6/10 by 1 users When the Cleveland Browns returned to the NFL, it was with the promise of bringing a winner to Cleveland. Instead, they became the worst team of the 21st Century. Details Casts Posters Images Title Dark Side of Football - Season 1 Episode 5 : Why Can't Cleveland Win? Alternative Titles First Air Date 2021-05-13 Last Air Date 2021-06-24 Number of Episodes 6 Number of Seasons 1 Genres Documentary, Networks Vice TV, Casts Plot Keywords , Episodes List Dark Side of Football Season 1 :Episode 1 Wide Receiver Divas Wide Receiver Divas 2021-05-13 Transgressions, crimes and scandals from America's most popular sport: football. Dark Side of Football Season 1 :Episode 2 The Dark Art of Bill Belichick The Dark Art of Bill Belichick 2021-05-20 Transgressions, crimes and scandals from America's most popular sport: football. Dark Side of Football Season 1 :Episode 3 Once a Raider, Always a Raider Once a Raider, Always a Raider 2021-05-27 Transgressions, crimes and scandals from America's most popular sport: football. Dark Side of Football Season 1 :Episode 4 Playing with Pain Playing with Pain 2021-06-03 Transgressions, crimes and scandals from America's most popular sport: football. Dark Side of Football Season 1 :Episode 5 Why Can't Cleveland Win? Why Can't Cleveland Win? 2021-06-10 Transgressions, crimes and scandals from America's most popular sport: football. Dark Side of Football Season 1 :Episode 6 FANatics FANatics 2021-06-24 Transgressions, crimes and scandals from America's most popular sport: football.