Kengo Legend of the 9

This achievement is the same as the online ones, only it's really like a training mode to test your guy out. To get this you first have to have completed a story with a character. It doesn't matter which difficulty you play on but you have to have the clear data. After that head to Solo Contest and pick the Five Man Contest selection.

You need to beat five enemies. I didn't get it until my fourth or fifth time, I was able to get to the fifth enemy every time but always ended up losing. I kept trying and I eventually got it. If you can't get to the last enemy consecutively, go through the game with another character and try it with them until you can do it.

I beat it with Miyamoto Musashi after going through the game on difficult.