In the 2005–06 season, Ovechkin and Crosby began their careers. In their first three seasons, they each won both the Art Ross and Hart trophies; Crosby captured both in 2007 and Ovechkin in 2008. The 2006 Stanley Cup Finals was the first time that franchises that originally played in the World Hockey Association (WHA) met in the Stanley Cup Final, as the Oilers lost a seven-game series to the Hurricanes. The following season, the Senators lost the finals in five games to the Ducks. The three year streak of Canadian teams in the finals was halted in the 2007–08 season, when the Red Wings defeated the Penguins for their fourth Stanley Cup in 11 years.
The success of the Heritage Classic led the NHL to schedule more outdoor games. The Sabres hosted the 2008 NHL Winter Classic on New Year's Day 2008, losing to the Pittsburgh Penguins in a shootout before a crowd of 71,217 at Ralph Wilson Stadium. The second Winter Classic was held January 1, 2009 at Wrigley Field in Chicago between the Blackhawks and Red Wings.
Intending to promote the game world wide, the league sent the San Jose Sharks and Calgary Flames to begin the 1998–99 season with two games in Tokyo, Japan. Since 2007, the NHL has been sending teams to Europe to start each season. The Los Angeles Kings met the Ducks at the O2 Arena in London, England to start the season the 2007–08 season. A year later, four teams were sent to Prague, Czech Republic and Stockholm, Sweden. One of those teams, the Rangers, also participated in the inaugural Victoria Cup, defeating the Kontinental Hockey League's Metallurg Magnitogorsk 4–3 in a single game. The NHL plans to have another four teams open the 2009–10 season in Stockholm and Helsinki, Finland. In 2010, Vancouver will host the Winter Olympics, the first time an NHL city has hosted the even since the league began participating. The NHL's participation in future games remains in doubt, as it has expressed a desire not to participate in the 2014 games in Sochi, Russia. The players, however, strongly favour continued participation in the Olympics. The third World Cup of Hockey is expected to take place in 2011, seven years after the 2004 tournament.