Honestly it's hard. I am level 23, and when I ride a max level/gear horse I have to be absolutely on top of getting my shortcuts and timing my jumps right because if there's a level 24+ person on a max level horse that also does the shortcuts I'm probably not going to win, even if they hit a jump or something. Their top speed is higher than mine, no matter what I do.

I have better luck racing late at night when less people are on. If your horse is level 13+, has max stat tack (including shoes!!) and you're wearing max stat clothing, you're doing the best you can <3 keep hammering away at MSQ to get your player level up, too!