Redman's professional career began when he was selected in the third round (75th overall) of the 2000 NFL Draft by the Baltimore Ravens. He was the third quarterback taken and one of the six drafted ahead of Tom Brady. Redman threw just 19 yards that year as he backed up Tony Banks and Trent Dilfer. Redman earned a Super Bowl ring that year when the Ravens won Super Bowl XXXV. In 2001, despite Banks and Dilfer both leaving, Redman did not play at all that year as veterans Elvis Grbac and Randall Cunningham took the snaps.