hammerman1 1) He's a good player, although he failed the last two times he played there. He's a good player, although he has failed the last two times he has played there. Both of these sentences are fine.
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hammerman11) He's a good player, although he failed the last two times he played there.Both of these sentences are fine. Long duration doesn't have anything to do with it.
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He's a good player, although he has failed the last two times he has played there.