I would think it depends on which way the head gasket is leaking. If coolant is going into the cylinders, it most likely won't pass because of the obvious white smoke and weird emissions that will produce. If it's leaking oil to the outside, I wouldn't worry, mine has been doing that for 7+ years and passed every New York inspection (finally getting that fixed this month). Oil into coolant, it may still pass.

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Streetside: 1987 Mercedes 300E Petrol Blue/Green
2014 Ford Mustang Grabber Blue
1999 Ford Ranger Green

Dockside: 1968 Eltro 17
1985 Silverton 34C