Two men play 5 games of checkers. Each man wins the same number of games. There are no ties. How is this possible?

“They both won 2 games each.”

If each man won the same number of games, they could not have played against each other and still have the same win count, as one would necessarily lose more games.

“They played in teams.”

The riddle specifies that there are two men, meaning they are individual players and not part of a team, which makes this scenario impossible.

“They played in a tournament format.”

A tournament format would imply they face different opponents, but the riddle implies that their games were only between the two men and no one else.