The 1999 Calder Cup Playoffs of the American Hockey League began on April 21, 1999. The sixteen teams that qualified, eight from each conference, played best-of-5 series for division semifinals and best-of-7 series for division finals and conference finals. The conference champions played a best-of-7 series for the Calder Cup. The Calder Cup Final ended on June 13, 1999 with the Providence Bruins defeating the Rochester Americans four games to one to win the first Calder Cup in team history. Providence's Peter Ferraro won the Jack A. Butterfield Trophy as AHL playoff MVP.