Street Fight? Guy with no gloves wins... you can grab, cause more damage and generally have more options available to you, guy with gloves essentially has pillows secured to his hands which really limit his options.

Boxing rules? Guy with gloves, the other guy will eventually break his hands or will have to limit his punches putting him at a disadvantage.

The boxer without may cause more cuts, but is apt to suffer hand and wrist injuries.

The boxer with gloves will have protected hands, and punches will hit as hard.

Depends on who can fight better

Whomever is the better pugilist (boxer).

Try it from both ends .... & you'll see