In 1979, the first of two times he would play on an AL pennant winner, Flanagan's 23 victories led the circuit and earned him the league's Cy Young Award. He was a member of the Orioles' World Series Championship team in 1983. He returned to Baltimore to close out his playing career as a reliever in 1991 and 1992. During this second tour, he contributed to the most recent no-hitter thrown by the club. He was also the last Orioles pitcher to appear in a major-league contest at Memorial Stadium.

This 11x14 photo was signed in black by Flanagan and inscribed, "Last Pitch 10/6/91." This item includes a Great Moments COA.