Second Serve (1986)

Fact-based story about tennis pro Renee Richards, whose player status was challenged in 1976 when it was revealed that she was a trans woman. Flashback to 1964 before she was out as trans, a successful New York doctor with a great lifestyle, a flashy girl friend, and a secret life. Her psychiatrist mother refuses to deal with her and sends her to a colleague who diagnoses with a psychotic gender confusion, which he says can be unlearned. After a failed marriage and parenthood, she comes out as trans, with a new life in California.

Unfortunately the movie Second Serve is not yet available on HBO Max.