Green’s Dictionary of Slang

boob v.²

to make a mistake, to blunder.

1910		L.A. Herald 18 Dec. 52/2: [cartoon caption] Yo’all Boobs. Stop yer boobin’.
1915		S. Ford Torchy, Private Sec. 284: Say, how about it, Miss Hampton? Suppose he hadn’t boobed it this way.
1919		T.A. Dorgan in Zwilling TAD Lex. (1993) 111: The Judge Boobed Another.
1921		T. Thursday ‘Hail the Professor’ in Top-Notch 1 Sept. 🌐 When a boob boobs his way in front of Doc Barnumbey with an act that looks high class and novel [etc.].
1935		T.E. Lawrence letter 4 Feb. in Garnett Letters (1938) 851: The camera seems wholly in place as journalism: but when it tries to re-create it boobs and sets my teeth on edge.
1946		G. Gibson Enemy Coast Ahead (1955) 193: The Pathfinder Force had boobed.
1953		P. Closterman (trans.) Big Show 42: Hell! The strategists had boobed.
1963–74		B. Humphries Barry McKenzie [comic strip] in Complete Barry McKenzie (1988) 24: This nut might boob on a retake.
1976		P. Theroux Family Arsenal 211: It all went disastrously wrong [...] Sweeney said, ‘You boobed.’.
1990		Beano Comic Library No. 190 38: Oh, no! We’ve boobed!

In phrases

boob up (v.)

to make a mess of (something).

1924		S.H. Adams Sailors’ Wives 228: Expert or no expert, you seem to have boobed up the case with special thoroughness.
1958		(con. 1945) F. Davis Spearhead 144: I really boobed things up.