Green’s Dictionary of Slang

1. to double-cross.

1863		T. Taylor Ticket-Of-Leave Man IV ii: The man who tries to double on me, had better have the hangman looking after him, than Jem Dalton.
1888		‘Rolf Boldrewood’ Robbery Under Arms (1922) 384: How did you find out Warrigal’s doubling on me?
1955		B. Hill Boss of Britain’s Underworld 3: I’ve always given everyone a square deal [...] not one crooked person in the world can say I’ve doubled on anyone.
2013		F. Bill Donnybrook [ebook] Ned had double-crossed Pete [...] He wouldn’t get a chance to double her.

2. (US) to double-date, i.e. for two couples to go out together.

1959		P. Roth Goodbye Columbus 95: ‘Ron and I hope that you and Brenda will double with us soon’.
1974		(con. 1960s) R. Price Wanderers 87: Hey, maybe we could double sometime.
1982		(con. 1970) J.M. Del Vecchio 13th Valley (1983) 469: We’re doublin with this dude who’s our star tailback.

3. to act as a double-agent.

2001

(con. 1964–8) J. Ellroy Cold Six Thousand 528: Lyle was doubling. He leaked some anti-Bureau shit to the House Judiciary Committee. Mr. Hoover had to pull a few bugs.

4. to double-park.

1995

S. Moore In The Cut 98: I have new words for the dictionary. [...] to double, to double-park.