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Parf of speech: Noun, OED Year: 1946, OED Evaluation: N/A

The pilot of an aircraft which is positioned behind and to one side of the leading aircraft, as in formation for combat; the aircraft itself.

Speaker: But, then, and I got older, then I n-- I went working for the hydro, ah, I went for the M-T-O, I was a wingman for a couple winters, you-know, part-time. Interviewer: What is, ah, sorry- Speaker: A wingman was, ah, at that time you had to have two in the truck when you were ploughing snow, the driver and then the guy operating the- the ploughs. I was in that ...
In a snowplow business, a plough operator who rides alongside the driver in the same car.