Season 2 Trevor was still getting back into his groove and would most likely lose to Sypha. He just wasn't as fast and stable as he is later.
Season 4 Trevor on the other hand became a tank with more tools. He survived an attack from death after fighting through all of Dracula's castle, had shrugged off hits from night creatures, and even was fighting while littered with needles in his body. He is likely going to survive a basic hit from her magic. She does have some stuff like her ice disc that could kill him though. If he has full equipment he is also going to be as tricky to fight as she is for him. His range with his morningstar is insane and likely going to one shot sypha and also his cross boomerang is going to do massive damage if he can land it on her as it sliced right through basically everything it touched. He has an advantage in both close range (killed a night creature with his bare hands) and long range (cross boomerang and somehow the morningstar which seems to have infinite range on it). She likely has the mid-range advantage with her tools but Trevor was always a master in working fights into where he was best. I'll go trevor 8-9/10 times.
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