NHL 2K8

Before you start your season/franchise you should edit rosters and trade all the top players (85+ rated) onto the team you intend to play with. Start the season and pick your stacked team. You should be able to sim the entire season and win the presidents trophy (awarded for having the most points in the regular season). I would sim 20 games, check the standings and save if you are still in 1st place overall. If you are not, then just reload your save and sim again. Once you complete the season with the most points save the game and sim through the playoffs. After each series you win, save again. If you lose a series reload your last save and re-sim it. Once you win all 4 series in the playoffs you will win the stanley cup. The achievement will then unlock.

Make sure you DON’T move the difficulty up or down on this one. I went from playing “Pro” to “All-Star” and the achievement didn’t pop all though I played almost all of the games.