The Date: April 2006
The Crazy Moment: During a match against Zab Judah, Mayweather was winning on all cards when Judah decided to throw a punch that was clearly below the belt. As a result, Mayweather's uncle/trainer Roger Mayweather entered the ring and got into a scuffle with Judah and his father/trainer Yoel Judah while Mayweather looked on.
Why It Was So Wild: This was a professional boxing match, yet it looked like something you'd see on a street corner late one Saturday night after everyone's had a few too many to drink. Roger Mayweather was fined $200,000 and suspended for a year for his participation in the fight and Judah was also eventually suspended from fighting for a year.