
This would be a very interesting fight to say the least. Both opponents are extremely acrobatic with their fighting styles, and both could sense the other’s next attack (either through the Force or via spider-sense).
Let’s get the obvious out of the way first. One would assume that Darth Maul would simply Force-choke Spidey and be done with him, but it’s been proven many times in the Star Wars universe, both in the movies and in its Expanded Universe, that it’s not as easy to Force-grab a skilled opponent who knows to keep moving… And if there’s one thing Spider-Man does during a fight, it’s move around.
While Spider-Man has the physical advantage over Maul, both in strength and agility, Darth Maul has his lightsaber, which I think gives him the overall advantage. Maul’s weapon would allow him to block and cut through Spider-Man’s webbing. Not to mention that as hard as Spider-Man punches, everyone should agree that a lightsaber cut is way worse.
This wouldn’t be an easy fight at all, but in the end I think Darth Maul would win by a very slight margin, because of his deadlier choice of weapon.
WINNER: DARTH MAUL