I had my arm broken while playing lacrosse but I know a guy who almost lost a ball after being kicked in the balls in TKD
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Not really sport... well ish... depending on your views of HEMA.
Top three painful injuries:
1: Got barged off my feet. The butt of the axe on my belt hit the ground, driving the head up into my ribs, cracking one, bruising two more. didn't really hurt bad at that moment (just knocked the breath out of me), but I just couldnt regain my breath, and the pain over the comming weeks was aweful.
2: A lad forgot to blunt the bottom spike of his axe and tried to hook my shield, instead he drove the sharp point into the back of my knee, and got it caught in the tendon.
3. Put on the tip of a boars snout (a wedge shaped shieldwall) at a full charge (about 12 vs 20). Crashed into the other shieldwall and the bottom of my own shield smashed down into my knee, displacing the knee cap. The enemy wall openned up infront of me (or was torn assunder depending on how you look at it) and the person I hit was flung a good 10 foot by the impact... and I still hobbled around and got a couple of hits in before they were all mopped up.
Got some other fun injuries but nothing as painful as those.1