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Ras has his sword
Matt as of Defenders with his billy clubs

Round 1: H2H
Round 2: Ras has a sword and Matt can use his clubs

Been some time since I checked Ra's feats, but I think he might take it. IIRC, he stomped Oliver when he was arguably in his prime and basically lost to plot during the finale. From what I can remember, he had Oliver disarmed and on his knees, but chose to do a villain monologue instead of finishing it, creating the opening for Oliver to steal the win. And he butchered Ollie during their first fight. Defenders Matt is an absolute beast as well though (holding off 2 Fingers of the Hand at once, hanging with Black Sky in H2H, holding the upper hand against Iron Fist during their brief clash etc.), so he will make him work for it.

Defenders Matt was a force. Toughness gets him through.