#9 Vince McMahon vs John Cena - Raw(27th March, 2006)
Now, this is just here for comic reasons, but it still deserves a spot. The Chairman of the board has had quite a few one-off matches. He has wrestled Brock Lesnar, CM Punk, Bobby Lashley and Kurt Angle among all people. But his most ridiculous match has to be against John Cena. John Cena had ascended to the main event level by 2006 and was the face of the company. Vince had a regular presence on TV back then and decided to insert himself into the storylines going into WrestleMania.
Cena was in a heated rivalry with Triple H who was his opponent for WrestleMania. Vince himself was fresh off of his match against Shawn Michaels and .... well, God himself. This is when the chairman decided to help his son in law against his rival and booked himself against his beloved champion.
A former WWE writer just went after JBL for his comments HERE
The match ended before anyone realized what happened as Triple H blindsided John Cena. Considering Vince and Cena have feuded multiple times since then, it is a surprise this match was their only encounter.