Easiest way to do this is in local versus (BATTLE > Vs. Player 2/Vs. CPU) against either a 2nd controller, or play against Easy AI in Versus mode. This will also be counted towards while working on Arcade Mode. Each individual fight will count as a match.
Just have to PLAY 5 matches not Win.
Can just spam the A button or use a turbo/chronus/titan to let the games play themselves if you want. Obviously must be done against the AI.