The fastest way to do this while still going for the other win achievements is to go to match creator for and edit an extreme rules match. Set steel chairs to be in every slot and have momentum charge set to fast alongside turning entrances and post match replay off. After that go to the game sliders and adjust AI reversals to low while setting every setting in the other two categories to max (especially the foreign object strength).
If you want to make this go even faster for things such as submissions (which you will do with breaking point maneuvers by holding the "A" button) create a superstar quickly that has minimum attributes and use a submission specialist such as Daniel Bryan against him. Now as soon as the match starts go outside of the ring and stand next to it. Hold LB to reach underneath the ring for steel chairs and select it by pressing "A". It takes 4 chair shots to break a chair so just keep pummeling away at your created superstar until you have broken 5 or so chairs (reaching underneath the ring for a new one every time one breaks). After that just toss him back in the ring and do a breaking point submission move. Click rematch quickly, rinse and repeat until you are done.
Check the video below for more information on how to do this.. This video WAS NOT MADE BY ME, all credit goes to the creator.