That would depend on what you'd call a "success."

But on the count I've gotten so far.... Once on the 3rd, once on his academy teacher, and if you count the "Harem no Jutsu" that would be three. I wouldn't count the time he took Konohamaru into the bathhouse as a success, as he got his ass kicked.

Hrm... now what would be a good question here...meh! Can't think of one, so here's an easy one. What was the name of the ninjutsu Kakashi used on Sasuke during their first training, after Sasuke used his grand fireball technique?