Mine did two to a point where kicking would be agony I now wear a support whilst riding and avoid doing riding after going for a run
I have a lot of back problems that also affect my legs and lately I felt that my left leg wasn't "working" and that compromises my riding and the way I work the horse. Since I started practicing Pilates, I feel much better and I have an exercise that I shoul do before I ride to "activate" my leg... it really works, it's amazing!! As a Pilates practitioner I recommend every rider to practice too to improve the resistance and health of our muscles and tendons
Hi! Do both of your ankles hurt when you jump? Does it happen too with other sports?
Maybe you have a weakness with your ankle, if you were injured once it is very possible that you are still weak now.
You can see a doctor to check if everything is ok.
You can ask your trainer if your position is great, if your knees are not gripped on the saddle for example
You have some stirrups that can help you, I love Flex On for that