Dodgeball Academia (UP)

At the beginning of the game shortly after the ceremony head to the top left of the school ground where there is some wooden steps leading up to a small building (Just left of the school and the locked gate, ball on the rail of the stairs).

On the top of these wooden steps stand on the left hand side and roll down (tapping B) towards your screen all the way down until you hit this bench and achievement will unlock. If you bump into anyone or the girl near the fence try again, keeping in mind you want to start at the top of the stair on the left hand side.

For a better understand see video at time 04:30 -

Start off entering the main grounds via the bridge from the leisure area. Roll to the right all the way to the fountain by the dome and smash into anything in that area. You can spam both B and RT (they do the same thing) instead of spamming the same button which can be difficult for some people. The achievement will unlock when you smash into something.

There is a ton of dialogue in this game so be prepared for a lot of reading or simply skip everything by double tapping
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Also not that once you initiate a fight you can go to (options/accessibility/difficulty) and from there make your damage taken 0% and damage dealt 400%
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Once you are able to reach the dormitory (where you sleep) start at the bikes to the left of the front door. Roll to the right and tap as fast as you can and got it my first try as the two sets of stairs really help you gain a lot of speed.

The best place I found to do this was in the school grounds. Just before the blue court in the centre where you first entered the school grounds, go either left or right as far as you can go then turn around and keep pressing B to keep rolling faster as long as you can until you hit something. If the achievement hasn’t popped then you will need to keep rolling faster and further until it does.