Wenger has never beaten Mourinho in 10 attempts and goes to Stamford Bridge tomorrow.
Hill-Wood told the Daily Star: "I think it would be a great achievement if Arsene can get his first win against Mourinho."
But he laughed off the idea of the outspoken and controversial Mourinho - who has often targeted Wenger in his attacks - ever taking the helm at The Emirates.
"I wouldn't find him at all easy as manager," he said. "I think it is most unlikely."
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