DALLAS (AP) — Jim Nill and Ken Holland were teammates in junior hockey nearly a half-century ago with big aspirations as players.

Their names are together on the Stanley Cup four times, not as players but rather for their front-office roles with the Detroit Red Wings during that run of championships from 1997-2008.

“We probably left three or four (titles) on the table. That’s how competitive it is,” Nill said. “But we had that good a team.”

Since they are opposing general managers in the Western Conference final, only one of the old friends will get the opportunity this season to maybe win another Stanley Cup.

“We know each other well, so it means a lot to come in here and play against him,” said Nill, who is in his 11th season as GM of the Dallas Stars.

The top-seeded Stars dropped the West final opener 3-2 in double overtime at home to Edmonton, where Hockey Hall of Fame member Holland is in his fifth season as general manager since the end of his 22 years in that same role with the Red Wings. Nill was his assistant GM in Detroit before getting hired in 2013 by the Stars, who are in their third West final in five seasons.