1) The man to win the tournament was John.
Can this sentence mean:
a) The man who won the tournament was John.
I am not sure that the two sentences mean the same thing. I think '1' places itself at a point of time before the end of the tournament and says that things indicated that John was destined to win the tournament. We don't know if he did or not. Maybe the tournament was cancelled. Maybe John was taken ill and could not continue playing etc. Maybe he did win the tournament.
My point is that to me the two sentences are not necessarily contradictory, but do not mean the same and would not mean the same even if we knew that John actually won the tournament. They are looking at an event from two different viewpoints.... I am not sure I am correct though. Maybe 'a' is one of the possible meanings of '1'.