I attack with a 5/5 creatured equipped with Umezawa's Jitte. He is blocked by 5 1/1's. He deals one damage to each of them. Does it get 10 counters or 2?
your creature only dealt combat damage once (to 5 different creatures). since your creature only dealt damage once, you only get one trigger. 2 counters it is
Lvl 2 Judge