I tried Ravioli's solution many times but couldnt get it to work. But then I tried this and got it on my first try:
Bases loaded. Have a fast runner on 2nd and 3rd and take a long lead towards home. Bunt towards first making the pitcher run towards the ball and he will then throw it home. As the throw goes home, steal additional bases. The guy going home gets called out but thats ok because the play is still going. When the catcher throws to second you have to send the 2nd man home (LB). He will either score cleanly or run into the catcher who will then drop the ball (which means he is safe at home.)
I tried this again after I got the achievement. The first time I ran over the catcher and the second time I scored cleanly. This is a much faster and less stressful way to get this achievement!!!