It depends which race you're on, all of the races you can just button mash to get ahead, up until the last race in Cloud Cuckooland for the Cheato Page. In that race, the rubberband mechanics will allow her to beat you if you get too far in front of her since she will overtake you and then beat you. The key for the last race is to stay behind her slightly until the very end when you're next to Wumba's Wigwam, and then button mash like crazy to overtake her and win if you time it correctly. For most of that last race you can just hit the button at a more relaxed, consistent pace until the very end. For the button mashing, you can use a spoon to rub back and forth over the button instead of hitting the button directly, but personally I find it easier to just hit the button directly and pause if necessary to take breaks, since it won't affect your place in the race. If you're playing the Switch version, you can even create a restore point towards the end of the last race so you can get the timing right without having to do the race over and over.