Alessandro Orlando (born 1 June 1970) is an Italian former professional footballer who played a defender.
A quick, talented, energetic, and dynamic offensive left-back, with a powerful shot and good technique, he excelled at providing long passes and crosses to forwards and at making attacking runs down the flank.
Despite his offensive and creative prowess, he was inconsistent at times, however, and was less effective defensively, as he often struggled in one on one situations with forwards.
A predominantly left-footed player, he was also an accurate free-kick taker.Although he was often a reserve player at Milan and Juventus, Orlando is one of the six players to win the Serie A title in two successive years with different clubs, winning the 1993–94 Serie A title with Milan, and the 1994–95 Serie A title with Juventus; the other five are Giovanni Ferrari, Riccardo Toros, Eraldo Mancin, Roberto Baggio, and Andrea Pirlo.