Green’s Dictionary of Slang

1. (Aus.) to deceive, to manipulate, thus tiddleywinking, corruption, deception.

1860		Twofold Bay Obs. (NSW) 7 Dec. 2/5: [W]e are all writhing under persecution. We’re [sic] been all humbugged and tiddleywinked with, particularly by the magisterial organ.
1861		Royal Cornwall Gaz. 22 Nov. 7/4: ‘Do you gain an honest livelihood; or do you live by ‘tiddley-winking’?
1874		Ballarat Star (Vic.) 2 Sept. 4/1: The Legislature have decreed before he can purchase the land he requires a sham process of selection must be gone through and hence the ‘tiddley-winking’ resorted to.
1880		Ballarat Courier (Vic.) 7 May 2/3: [B]y a little tiddleywinking, the wire-pullers managed to defeat the decree of a majority of the manufacturers' committee on this subject.

2. (Aus.) to act illegally, to bend the rules.

1860		Argus (Melbourne) 20 Apr. 5/1: The process by which these false measurements were successfully effected is known [...] as ‘tiddley-winking;’ and [...] it is clear that the whole essence of this contract has consisted in ‘tiddley-winking.’ Not only [...] has this country been charged for metal to the amount of £20,000 more than it has received; but every portion of the railway work is faulty, or rotten, or dishonest.
1870		Geelong Advertiser (Vic.) 5 Sept. 3/3: The perpetrators of that piece of ‘tiddley-winking’ [...] got six months for their pains.
1908		Truth (Perth) 13 June 3/6: Did you not bear that some tiddley-winking had gone on between Salter and Jessop? - No, if you mean by tiddley-winking that Salter robbed Jessop, it’s a lie. I know Salter too well.
1912		Eve. News (Sydney) 20 Mar. 7/5: North Ward aldermen had no money. Anyhow, they would like a finger In the pie before it was baked. Alderman Hardy thought there was too much tlddley winking.

3. to fiddle around with; thus tiddleywinking n.

1861		Age (Melbourne) 1 Oct. 5/1: [N]othing but the term ‘tiddley winking’ could express the idea the woman's behaviour created.
1871		Aus. Town & Country Jrnl (Sydney) 9 Sept. 24/2: As it was the race was nearly lost through tiddly-winking with a brute like Vauban, who couldn’t win a race with a racehorse in a twelvemonth over Randwick.
1888		‘Rolf Boldrewood’ Squatters’ Dream in Farmer & Henley Sl. and Its Analogues VII 884/1: I wonder what old Morgan would say to all this here tiddley-winkin’ with steam engine, and wire fences.
1892		Sth Aus. Register 20 July 2/2: Now Henry Lamshed has come here there will be no tiddleywinking.
1908		North West Post (Formby, Tas) 13 Oct. 4/1: The town ratepayers of Devenport are determined no ‘outsider’ shall have anything to do with their waterworks, electric light, or other town works, and they will not permit any tiddle-winking with their funds.
1915		Hamilton Spectator (Victoria) 12 Feb. 4/3: They had been ‘tiddley-winking’ with by-laws for many years.

4. to drink.

c.1910

Atkins & Dwyer ‘Don’t I Wish I Had ’Em’ 🎵 Her Father can’t he tiddley-wink - he's only happy when in drink.