[Rooish]

The major one I can remember is from the original Mirage comics, in "Return to New York, Part 1." This is a very key issue, as it was written by Eastman and Laird, and Eastman did the layouts, and it's one of the major emotional episodes in the series.

Leo and Raph start fighting when Leo holds a wooden practice sword in front of Raph to prevent him from leaving, and Raph starts trying to grab the sword in a fury. Initially Leo knees Raph over, and then they fight more and Raph kicks Leo over. Leo trips Raph, then climbs on top and holds his practice sword against Raph's throat; Raph grabs the sword and punches Leo off, and Leo grabs Raph in a headlock, which Raph struggles out of. Then Raph picks Leo up and throws him through a wall. So the pretty clear winner in this fight is Raph. I think this is a testament to Raph's physical strength, as he can pick up Leo above his head and throw him. (Although it was not shown if Leo could have done the same thing.)

Although this issue had Raph win the fight, I'm not saying that Raph is the "better fighter" (I don't think he is, although this is an argument that seems to have sparked some serious anger in these forums before). But this is the one big Leo-Raph fight I can remember from Mirage. Later in the "Return to New York" saga, Leo saves Raph's life from a bunch of Elite Ninjas--although Raph was caught offguard in that fight, and Leo caught Raph's attackers offguard when he saved Raph. The Leo took on the Shredder, and we didn't see how well Raph would have fared there, because Raph wasn't involved.

In the new 'toon, in one of the episodes... "The Shredder Strikes," I think, Leo and Raph have a scuffle and Leo wins by throwing Raph off a rooftop... accidentally, I presume. In the new series I think Leo's position as "best fighter" is definitely played up. But anyway, from the original comics, at least in that circumstance, Raph was the winner in a one-on-one fight against Leo.