#6 Kevin Owens
Although it was brief, Owens has stood across the ring from 'the Chairman'. It was during Owens' run on SmackDown where he and AJ Styles were feuding over the United States Championship. Shane McMahon was still the Commissioner of SmackDown but was getting involved in the feud between Owens and Styles.
After Owens had enough of Shane's involvement, he was eventually confronted in the ring by Mr. McMahon. As he usually does, he talked down to Owens and said that both he would be facing Shane in a Hell in a Cell match at the following PPV.
Before Vince could leave the ring, Owens attacked 'the Chairman', both headbutting him like in the above photo while also laying him out after a frog splash from the top rope. When everything was said and done, Vince was left with some blood on his face.
If you don't remember, Owens won the Hell in a Cell match after Shane jumped off the top of the cell and Sami Zayn pulled him (Owens) off of the announce table. While the encounter may have been short, Mr. McMahon stilled interjected himself into Owens' business.