The Wicked Reporter 3: The One That Got Away (1996)

A couple years have passed, Matsuzaki is divorced and has a daughter and is still up to his old compulsive gambling, boozing and womanizing even as he stares middle age in the face. At his daughter's school he meets a teacher who's similarily obsessed with horserace betting and who's also frigid - something he does his best to therapize. He also reconnects with his ex-wife, who just so happens to be the literary agent and love interest of another writer of the gambling genre. An epic gambling battle between the two ensues.