Green’s Dictionary of Slang

head v.1

[the betting on ‘heads or tails’]

1. to play ‘two-up’.

[Aus]Dead Bird (Sydney) 9 Nov. 6/2: No sooner are the crowd set down [...] than a ‘two up’ or ‘heading ’em’ school starts.
[Aus]Dead Bird (Sydney) 17 Jan. 1/2: Taught Juno to ‘head ’em’ and Doto to dance.
[Aus]Argyle Liberal (NSW) 7 Nov. 2/4: I approached him while Bob went in the direction of Ready, who was engaged ’eaden ’em with one of the young R—’s.
[Aus]C.J. Dennis ‘A Spring Song’ in Songs of a Sentimental Bloke 15: Jist ’eadin’ ’em, an’ doin’ in me gilt.
[Aus]Truth (Brisbane) 11 Jan. 11/6: [headline] IS TWO-UP TWO-UP WHEN IT’S CALLED HEADING ’EM?

2. (Aus.) to toss up for.

[Aus]Dead Bird (Sydney) 24 Aug. 7/2: He headed the boys for the bundle and came out half a caser a head.

3. to throw ‘heads’ in a game of two-up.

[Aus]L. Glassop Lucky Palmer 100: And he’s — headed ’em!