July 9, 1999 : Wings signed unrestricted free agent Ken Wregget
July 15, 1999 : Detroit Red Wings signed free agent goalie Manny Legace to a multiyear contract Thursday.
August 4, 1999 : Bill Ranford signed as an unrestricted free agent with the Edmonton Oilers
September 27, 1999 : Detroit Red Wings placed Manny Legace on waivers.
September 29, 1999 : Detroit Red Wings lost Manny Legace to the Vancouver Canucks on waivers.
October 14, 1999 : Detroit Red Wings reacquired Manny Legace from the Vancouver Canucks.
November 25, 1999 : Wings recalled Aren Miller from the Cincinnati Mighty Ducks.
December 2, 1999 : Chris Osgood was placed on injured reserve with a fracture of his right hand suffered November 24 vs the St.Louis Blues.
December 2, 1999 : The Wings have recalled goaltender Manny Legace from the Manitoba Moose and reassigned goaltender Aren Miller to the Cincinnati Mighty Ducks.