I have so many awesome sports injuries, but the thing that hurt the most wasn't one of them.
I shattered my ankle (Jason Kendall style) going 1st to 3rd on a single. My coach was saying down, then the ball went airmail and he said up. SO I planted my foot and tried to pop up on the bag and turn home, my cleat got caught under the base and the pop up safety feature failed. One shattered ankle.
I broke my wrist and gave my self a concussion in warm-ups. I had just switched from JV to Varsity, and in JV i played centerfield, but on V i was playing right field. Our stadium has 420 center field wall, and a 315 right field wall. The coach blasted a drive over my head and I just turned and ran for it. I dove right into the foul pole, first my glove hit and broke my wrist. Then my head hit and knocked me the hell out.
I broke a few ribs in football, dislocated my shoulders about 7 times (3 times in one game my senior year, which ended up being me last game ever). Broke some fingers, sprained some stuff.
I walked on to the Ball State football team in 2004. I was playing great in the preseason, and was already lining up at 2nd team linebacker. There was a freshman tight end (Darrius Hill, he is in and out of the NFL) who was a jacked up receiver and didn't really know how to block. He chopped the hell out of my knee and shredded the ACL, MCL and PCL. I never really made it back from that one.
But the worst pain I have ever had was a fluke. I woke up one day and had a really sharp pain in my gut. I thought I just needed to shit. I went on with my day, even though it was horrible pain. The next morning I woke up and I couldn't move. Moving any part of my body would shoot a horrible pain into my gut. I had to wait until my little brother got home from school, made him pick me up and put me in the car and drive me to the hospital. I went right to the ER and they pumped me with some bad ass pain killers. They thought I needed to get my appendix out, so they took an MRI and did some other stuff. I was getting prepped for surgery when a different doctor stormed in and said "It's not his appendix, get him back in his room."
What happened was there are these flanges, pieces of fatty tissue, that hang off your colon. Two of mine twisted together and shut off circulation to my entire digestive tract. They just kept me in the hospital until the flanges untangled.
Worst pain ever.