Broke my ankle (playing basketball) during my sophomore year of high school. Missed the whole basketball season. Was going to play varsity that year.
Cut tendons in hand moving furniture for a friend. My elbow broke the storm glass door moving a couch and instead of dropping the couch I set in down and the back of my left hand went right into the cut glass remaining in the door. That happened just before my senior year basketball season. Missed several games with that injury.
Had a bad ankle sprain playing softball one year. Hurt just bad and took the same amount of time to recover as the broken ankle. Did that when I was 24 years old.
But, the most debilitating (not as painful though) sports injury by far has been dealing with both lateral and medial epicondylitis (tennis and golfers elbow). Won't go into detail, but that injury has sidelined me way longer than the other injuries.
I will say this. The first time I got epicondylitis the doctor sent me to a physical therapist. The physical therapist told me right away that I'd been better off (healing wise) if I had broken my elbow. 15 years later he was proven right, many times over.