Green’s Dictionary of Slang

1. a watchman.

c.1786		Grose Classical Dict. of the Vulgar Tongue ms. additions n.p.: Pilot, a Watchman.
1821		Egan Life in London (1869) 113: I [...] must have foundered had it not been for the assistance of a pilot, who safely towed me into the light-house.

2. (US) a cabdriver.

1899		W.J. Kountz Billy Baxter’s Letters 71: We made a bargain for a dollar and a half the first hour and a dollar each succeeding hour, and then we fell in and told the pilot to take us all over New York.
1936		Charleston (WV) Daily Mail 9 Oct. 8/8: If you happed to climb into a cab manned by a particularly talkative pilot there is some comfort in knowing that the boys in the profession would dub him ‘a coffee-pot lawyer.’.

3. (orig. Aus.) a jockey.

1887		Sydney Referee 19 May 5/4: Consequently it redounds more to his credit, and his pilot is positive that he is capable of even performing better things with him, did his business enable him to prolong his stay.
1901		West Australian (Perth) 13 Apr. 12/1: As a light-weight pilot Derry Dalton stood high in public estimation.
1907		Sun. Times (Perth) 2 June 10/5: She [i.e. the horse] had greatly disturbed the equanimity of her pilot by her friskiness and her cursed persistence in fighting for her head.
1966		J. Holledge Great Aust. Gamble 16: And in the Cup its pilot was not Pike but the much lighter Bob Lewis, the same jockey who had lent Connolly 30 shillings back in 1895.
1976		Horse and Hound 10 Dec. 41/1: He was to underline his Epsom misfortune by streaking home in the Irish Sweeps Derby, when his French pilot was replaced by Geoff Lewis [OED].
1996		J. Byrell Lairs, Urgers & Coat-Tuggers 70: W. ‘Billy’ Williamson [...] just happened to be among Big Oscar’s favourite six pilots.

4. (Aus.) any form of ‘driver’, e.g. of a food or drink cart.

1914		Sport (Adelaide) 12 June 4/1: Jimmy H., the lemonade cart pilot, tells a story [etc] .
1914		Sport (Adelaide) 3 July 4/5: Jim S., the ice cart pilot .

5. (US black) a bandleader.

1934

M. Fulcher ‘Believe Me’ in Afro-American (Baltimore, MD) 22 Dec. 12/3: Jessie Mann [...] and an orch pilot’s soror.

6. (W.I.) a procurer.

1939

A. Durie One Jamaica Gal 55: Phoebe [...] paid a tout or ‘pilot’, named Josiah to accost sailors when they came ashore.

7. see skypilot under sky n.¹