Anderson and Alucard weren't well-matched, they just had similar personalities.
OK this is how things would roll. Alucard wants to die, especially by human hands. Therefore, Guts would be the perfect means. He would toy with Guts, give him lots of chances to win, and Guts probably would win because Alucard let him.
But god knows how he'd even do it, and in the end Alucard would probably only be weakened temporarily until can no longer attack.
Could Alucard kill Guts? With enough effort, probably. Therefore, ALUCARD WINS.