1988, February During the video speech for the "Irish Award" she was given 1988, May 24 Madonna - Ciao Italia: Live From Italy is released on home video 1988, June 5 Going to the Tony Awards After Party 1988, July 5 Leaving The Royale Theater After a Performance of Speed the Plow 1988, August 16 Madonna and Sean celebrate her birthday and their wedding anniversary at a private party in New York 1988, September 11 Participating in Sport Aid 88: The Race Against Time marathon in New York

1988, March Beginning rehearsals in New York for David Mamet's play Speed-The-Plow 1988, May 26 Going to the Sandy Gallin's Birthday Party 1988, June 16 Leaving The Royale Theater After A Performance of Speed the Plow 1988, July 12 Leaving The Royale Theater After a Performance of Speed the Plow 1988, August 17 Arriving at The Royale Theater For A Performance of Speed The Plow 1988, October Visiting the Bryan Ferry tour concert

1988, May 3 Speed-The-Plow opens on Broadway at the Royale Theatre in New York 1988, June 4 Leaving The Royale Theater After A Performance of Speed the Plow 1988, June 27 With Sean attending the Mike Tyson vs Leon Spinks heavyweight fight at Trump Plaza Hotel & Casino 1988, August 2 Arriving to The Royale Theater to perform In Speed the Plow 1988, August Appearing in a tv add to support "Safe Sex Campaign" 1988, November 16 Attending the opening night of Hurly Burly at the Westwood Playhouse

1988, May At the premiere After Party Madonna talks to various tv media 1988, June 5 Presenting a special award to the founders of the South Coast Repertory of Costa Mesa at the Tony Awards 1988, July 1 Making a surprise appearance on Late Night With David Letterman 1988, August 11 Leaving The Royale Theater For A Performance of Speed the Plow 1988, September 4 Madonna plays her final performance in Speed-The-Plow on Broadway 1988, November 31 Madonna and Sean are officially separated and will begin divorce proceedings