The May 16, 1999 Edition of Maryland Championship Wrestling took place in Owings Mills, Maryland.
- Numbers in parentheses indicate the length of the match.
- (c) refers to the champion(s) heading into the match.
- Christian York (c) defeats Joey Matthews and Rich Myers (w/ Platinum Nat) in a Three Way Elimination Match to retain the MCW Cruiserweight Championship (9:06)
- Head Banger Mosh (c) defeats Jimmy Cicero (w/ Romeo Valentino) to retain the MCW Heavyweight Championship (7:35)
- Guy Pritzker & Justin Ott (w/ Sharon Lilly) defeat Dino Divine & Mark Shrader (w/ Cueball Carmichael) (14:27)