Green’s Dictionary of Slang

in a problematic, difficult manner.

1791		H. Lemoine ‘Education’ in Attic Misc. 116: Nor could she lounge the gagschule for a win, / The knowing Bench had tipp’d her buxer queer.
1833		‘Dick Hellfinch’ in Rummy Cove’s Delight in Spedding & Watt (eds) Bawdy Songbooks (2011) III 105: [as 1791].
1880		E.J. Milliken ‘Cad’s Calendar’ in Punch Almanack n.p.: Lots o’ larks that empty pockets ‘queer.’ / Can’t do much on fifty quid a year.