Green’s Dictionary of Slang

lolly n.4

[? rhy. sl. )lollipop = cop = copper; or Rom. loli/lullo, red (note Roma use of lolli, a farthing/copper coin]

money; also attrib.

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[US]Wash. Times (DC) 21 Aug. 4/4: Be careful how you track with those lads who spill that lolly lingo and don’t show any signs of support! When a guy sounds too good to be true, beat it!
[UK]M. Harrison Reported Safe Arrival 61: This ’ere bloke touches the Guv’ment fer a nice drop er lolly.
[UK]J. Arden Live Like Pigs XII: sailor: A man can work and he gets glory, right? / rachel: He gets lolly too, boy.
[UK]B. Reckord Skyvers I ii: I like ’em thirty, thirty-five, even forty like; get a bit of lolly and a lot of fun out of ’em, see?
[UK](con. 1960s) Nicholson & Smith Spend, Spend, Spend (1978) 95: Look at all that lovely lolly.
[Aus]M. Bail Homesickness (1999) 170: The real lolly was in the Atlantic run.
[UK]D. Lodge Therapy (1996) 110: When it was a runaway success she was pleased [...] for the sake of the lolly.
[Aus]J. Byrell Lairs, Urgers & Coat-Tuggers 203: ‘I’m willing to sling each of yer, say, forty quid so you can then say you did not do all your lolly’.
[UK]K. Sampson Outlaws (ms.) 37: Ritchie Mahon and co. are half thinking they wouldn’t mind an instant return on their lolly.
[UK]K. Sampson Killing Pool 80: [...] full of beans after successfully switching a bumper load of drug lolly.

In compounds

lolly night (n.)

(N.Z.) the evening of pay day, which brings with it the expectation of picking up a sexual partner.

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[NZ]McGill Reed Dict. of N.Z. Sl. 129: lolly night, the expectation of sexual fulfilment on pay day.