Green’s Dictionary of Slang

1. to confuse, to discomfit [SE pull the wool over someone’s eyes].

1845		J.J. Hooper Adventures of Captain Simon Suggs (1851) 62: At last he thought it best to return to the ‘ten’ upon which he’d bet five hundred dollars. ‘Now, I’ll wool you,’ said he.
1851		‘Losing Game of Poker’ in Burke Polly Peablossom’s Wedding 46: I’ll git Smith to playing, and if I don’t wool him, then my name ain’t Bennett.
1881		Bulletin (Sydney) 21 May. 9/2: He was ‘woolling’ his head to find a rhyme for ‘bronchitis’.

2. (US) to pull someone’s hair in play or anger; thus woolling n. [wool n.¹ (2)].

1931		D. Runyon ‘Lillian’ in Guys and Dolls (1956) 239: Lillian is not such a cat as will stand for much woolling around.
1953		Randolph & Wilson Down in the Holler 300: Them kids is always a-woolin’ the baby around, pullin’ its hair an’ rollin’ it in the dirt.
1987		(con. 1930s) L. Redmond Emerald Square 140: ‘What did you expect him to do?’ said my mother unexpectedly. ‘Stand there and let you wool the head off him?’.