Green’s Dictionary of Slang

1. to swindle, to cheat [? misprint or mis-reading for bubble v.¹ ; Partridge cites a correspondent who found ‘an “indignant gentleman captain” writing to the Navy Board’ c.1688 and using the word, but SE bobble, to bob up and down, has not been found until 1812].

1984

Partridge DSUE (8th edn) 107/2: ca. 1660–1720.

2. (US Und.) to excite a victim’s suspicions, esp. when passing them short change.

1940		D. Maurer Big Con 290: To bobble. To excite a mark’s suspicions, especially while short-changing him.
1962		S. Longstreet Flesh Peddlers (1964) 167: Imagine that swine Boley letting a deal bobble.

3. (US) to make a mess of, to fail.

1972

R. Kahn Boys of Summer 136: I had no stomach to be quizzed on my bobbling of the Robinson story or on the Herald Tribune’s sudden censorship.