One More Thing: dunno if it's a record, but with Cruz's win Woody Allen has now directed someone to a supporting acting Oscar *five* times. He's done it with Dianne Wiest (twice), Michael Caine and Mira Sorvino. Next year? Well, Patricia Clarkson is in his new one and she's surely due.
Speaking of, I saw in the "coming attractions" clips that Hilary Swank is playing Amelia Earhardt -- and every time Swank plays a butch woman she wins an Oscar. You've been warned...
Allen is an Oscar machine.
He has rec'd 21 nominations, including 14(!) for Original Screenplay, which must certainly also be a record, and won twice. He has 6 Best Director nominations & won once (for
Annie Hall, which also got Best Picture), and in what must surely be yet another record, his other 5 Directing nominations were for films that
weren't nominated for Best Picture. He has directed 16 actors to nominations (if that's not a record he must be close) and they've won 6 times (12 Supporting noms including the 5 winners you mentioned + 4 Leading Role noms including Diane Keaton's win for
Annie Hall). He has rec'd writing nominations in 4 straight decades & directed an Oscar winning performance in 4 straight decades.
One of these days someone is going to start calling him the best director of all time, if only to start an argument.
(paging Mick LaSalle!)