MLB The Show 17

This is probably the most frustrating trophy to acquire in this game especially if you are not good playing online against people. You will need to get 3-5 wins in Diamond Dynasty online to get enough points to get places into the Regular Season (200+ points). You accumulate points with every win. Losses do not make you lose any points. That is the only good thing about it. But this will reset with each season. The current season ends on May 15th.

Just to warn people - I'm a few wins away from this trophy, but it is very annoying to boost. It is easy to initially match up with your partner, and for one of you to throw the game - however, I believe the matchmaking algorithm doesn't want the same people facing each other multiple times. After I face that person once, we haven't been able to find each other again when searching for an opponent. Considering the server is practically empty - I doubt that's the issue. The only solution I can find so far is creating a load of alternate accounts and throwing the games with those with your partner if you want to boost online. Quite annoying.

Edit - You can face the same person, but only on a new day.