Shanahan finished off the 1996–97 season with his usual productivity, scoring a total of 47 goals for the season, and also being named to the 1997 NHL All-Star Game. In the 1997 playoffs, he also contributed with nine goals and eight assists, helping the Red Wings to their first Stanley Cup since 1955. They repeated as Cup champions the next year, despite an off-season for Shanahan in which he managed just 57 points. The following season, in 1998–99, Shanahan continued at that pace with 58 points, but was still invited to another All-Star Game. Entering the 1999 playoffs as back-to-back Stanley Cup champions, the Red Wings were eliminated by the rival Colorado Avalanche. The next year, in 1999–2000, Shanahan scored 41 goals, indicating a return to his usual form, however the Red Wings were once again eliminated by the Avalanche in the 2000 Playoffs. After the season, he was named to the First All-Star Team for the second time in his career. He followed up his resurgent season scoring 76 points in 2000–01, although Detroit were upset in the first round of the 2001 playoffs by the Los Angeles Kings.