Diner Dash

There aren't enough players online to gain this legitimately so chances are you will need to boost this, you will need 2 people to get it. Create a private match set to Tip Wars, $5000 and invite your friend in. Your best bet to make this go quicker is to use the restaurant Vishnu's Garden Café and use the combo method listed for the "I really ate the whole thing" trophy. You must play out the entire game (I tried quitting out, and even though it shows a win, it does not count). Have whoever is working on their win score $5000 as fast as they can, if you utilize the combos these should take around 2 minutes a game. Rinse and repeat 9 more times.

Find boosting partners here: LINK