Gintama - Season 4 Episode 5

Hasegawa is tired of alway losing and being called a Madao, so together with Gintoki they bet on horse races. After many failures, Hasegawa tells him of his effort to leave the "Madao Spiral", unfortunate turn of events that happened since he gained the nickname. Together with Gintoki Madao decides to try one last time, betting on the horse Justaway. In the middle of the race Gintoki tells him that he bet on another horse and after a head on head race between Justaway and Gin's horse Cheap Impact, it seemed at first that Justaway won but then it got disqualified and Cheap Impact won instead. But by that time Gin has already shred his ticket into pieces and neither of them won.