Now, each will have to defeat the other to do it.
When Cooper's Tampa Bay Lightning play Bowness' Dallas Stars in Game 1 at Rogers Place in Edmonton on Saturday (7:30 p.m. ET; NBC, CBC, SN, TVAS), it will be the first time a coach and his former assistant will face each other in the Stanley Cup Final.
Bowness was an associate coach on Cooper's staff for five seasons with Tampa Bay, including the 2015 Cup Final against the Chicago Blackhawks, which it lost in six games. They split after the Lightning lost to the Washington Capitals in the 2018 Eastern Conference Final.
"We spent half a decade together and we had some pretty good runs, especially the one in 2015, and [Bowness] was a big part of it," Cooper said Friday. "Then, eventually you part ways. It was amicable, but in this league as you see, coaches change teams all the time, and sometimes there's [a need] for a fresh start, and probably for both of us that was needed.
"But I'm probably not sitting here today without a lot of that help of Rick Bowness."
Cooper was a first-time coach in the NHL in 2013 when he was looking for someone who knew the League to help him behind Tampa Bay's bench. Bowness, who had recently been let go as an associate coach with the Vancouver Canucks, had plenty of experience.
Bowness played six seasons in the NHL (1975-81) as a gritty forward with the Atlanta Flames, Detroit Red Wings, St. Louis Blues and Winnipeg Jets. The oldest coach in the NHL at 65, he has worked 38 seasons in the League as a coach, associate or assistant (1984-present) with the Jets, Boston Bruins, Ottawa Senators, New York Islanders, Phoenix Coyotes, Canucks, Lightning and Stars.
"Going through the hiring process, it was about bringing somebody in that knew the League and, honestly, could work a little bit as a mentor for myself," Cooper said. "That's what I personally wanted and searched everywhere and was very fortunate to run into Rick Bowness because he was kind of in between organizations at the time.
"I learned so much from him just about how the League works and how to have success in this league."
After Bowness moved on from Tampa Bay, Dallas hired him as an associate to be a mentor for coach Jim Montgomery, who joined the Stars in 2018 as a first-time NHL coach following five seasons coaching the University of Denver men's team. But when Montgomery was fired for unprofessional conduct Dec. 10, Bowness suddenly found himself as an NHL coach for the first time since 2003-04 with the Coyotes.
The Stars were 20-13-5 under Bowness and are 13-8-0 in the postseason, advancing past the Calgary Flames, Colorado Avalanche and Vegas Golden Knights to reach the Cup Final.
"We had five very good years," Bowness said of his time with the Lightning. "… We got the team back to the playoffs after they had missed. We went to three conference finals. We went to the Final in 2015. So they were five great years, but as a coach, there comes a point when it's time to move on, and I was ready to move on.
"It was a split that was good for both of us. I was ready to move on. They were ready to move on. So no hard feelings. That's hockey."
