Not unless this counts, when he and Gohan came out of the Hyperbolic Time Chamber and talked to her, tapped her on the shoulder and she went into the wall, getting hurt. but that was によって accident.
孫 悟空 had hit chichi, but not in purpose. I think the first one was when 孫 悟空 came back from Yarddrat- planet and he asked Chichi to allow Gohan to be trained for the androids. 孫 悟空 just 発言しました with a smile: "Oh come one." And he hit Chichi's back but cause 孫 悟空 didn't estimate his powers he hit accidently her through the wall, 木, ツリー and the 次 stop was her head in the rock. ^_^
