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1.
this refers to the name that Matt Bailey received in early September of 2009. He goes by Bossman Bailey when he defeats less competent people in bowling by one pin, even though it was only the fourth time the Bossman had played in his life. The Bossman Bailey rules over The Boss and all other Boss-like references
Mason: your a bitch!!!

Bailey: you can call me Bossman Bailey!
by dragonbasketball43 October 05, 2009
3 0

Words related to Bossman Bailey:

bailey bossman bowling bitch boss bossin weakling
 
2.
A bitch that narrowly beats out a superior player in a game of bowling.
Cody: I cannot believe he just beat you, and by one point!

Carson: I know, he's Bossman Bailey.
by The One And Only Pussymonster October 07, 2009
1 3