Piccolo - end of Dragon ball/ beginning of Dragon ball z (manga vol 16-17)
Piccolo - Saiyan Saga
Piccolo - Frieza Saga (fused with Nail)
1st one Piccolo will lose since I assume this is EoS Yusuke as the Op never specified. 2nd Piccolo might lose, though it'd be tough. He's a moonbuster, though Yusuke is a world-ender here as S-class. 3rd, Piccolo stomps utterly. There is no question here.
1. Piccolo was Moon busting here he stomps
2. Piccolo was stronger than he was in the beginning of the series he stomps harder.
3. Yusuke just bends over and tells Piccolo to be gentle.
Yusuke loses all three rounds. Piccolo is a casual moon-buster in the first two rounds and a planet-buster in the final round. That puts him beyond Yusuke's abilities by a lot. The cast of Yu Yu Hakusho have a lot of "flashy" power. They have a lot of flash and flare but in terms of POWER power they fall well short of dragonball. I see even Yusuke's most powerful rei gun being smacked back right into his face.