The season was the first since to the 2004–05 lockout in which every team played each other at least once during the season, following three seasons where teams only played against two divisions in the other conference (one division at home and one on the road). It began on October 4, with the regular season ending on April 12. The Stanley Cup playoffs ended on June 12, with the Pittsburgh Penguins taking the championship. The Montreal Canadiens hosted the 57th NHL All-Star Game at the Bell Centre on January 25, 2009, as part of the Canadiens' 100th season celebration.
Increase in salary cap
National Hockey League announced that the regular season salary cap would be going up for the fourth straight season. The 2008–09 salary cap is being increased by $6,400,000 (US) per team to bring the salary cap up to $56,700,000 (US). The salary floor is at $40,700,000 (US), which is higher than the salary cap on 2005–06 season.
The NHL brought in a number of rule changes for the start of the 2008–09 NHL season aimed at increasing offence and safety. The first rule change was to Rule 76.2 on faceoffs. The first faceoff of a power play will now be in the defending zone of the team that committed the foul, regardless of where the play was stopped. The second rule dealt with the issue of safety while players are pursuing the puck on a potential icing call. Rule 81.1 states that, "Any contact between opposing players while pursuing the puck on an icing must be for the sole purpose of playing the puck and not for eliminating the opponent from playing the puck. Unnecessary or dangerous contact could result in penalties being assessed to the offending player." The third rule change also dealt with faceoff position: if a puck is shot off the goal frame, goal post or crossbar, the subsequent faceoff will remain in the end zone where the puck went out of play. Another rule change prohibits TV commercials, game breaks, and any line changes immediately after an icing call.
The 2008–09 schedule returns to the pre-lockout schedule. The new schedule eliminates the three-year rotation where teams would only play teams in two of the three divisions of the opposite conference; instead the new schedule guarantees that each team plays every other team at least once. In this new schedule, each team will play their divisional rivals six times for a total of 24 games; they will play all other conference teams four times for a total of 40 games, and will play every team in the opposite conference at least once for a total of 15 games. To obtain a total of 82 games there are an additional three-wild card games; for the Canadian teams, the three-wild card games are composed of playing the three Canadian teams in the opposite conference an additional time.
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National Hockey League to open 2008–09 season in Stockholm and Prague
The regular season started with four games played in Europe. The Ottawa Senators and the Pittsburgh Penguins played each other twice in Stockholm, Sweden with the two teams splitting a 2-game premiere, and the New York Rangers and the Tampa Bay Lightning played each other twice in Prague, Czech Republic The Rangers swept Tampa Bay 2–0. The New York Rangers represented the NHL in the inaugural Victoria Cup challenge game as part of the club's pre-season schedule. The four teams also played some pre-season exhibition games in Europe.
Other than the four overseas regular season games starting October 4, October 9 was the actual first day of regular season games as far as widespread continental North American broadcast from most providers, including pay per view hockey packages. Other teams still played preseason games between October 4 and 6.
By February 23, 2009, all four teams who started the season in Europe had fired their coaches.
Main article: 2009 NHL Winter Classic
Because of the success of the 2008 Winter Classic, another outdoor game was held in the 2008–09 NHL season. While Yankee Stadium was considered an early favorite, in a game to be hosted by the Rangers, cold-weather issues involving the old stadium put that location out of the mix. Another site considered was Beaver Stadium at Penn State University, with that game to likely involve the Penguins and the Flyers.
On May 29, 2008, TSN reported that the 2009 NHL Winter Classic would be held in Chicago, Illinois on January 1, 2009, played between the Chicago Blackhawks and defending champion Detroit Red Wings. Soldier Field was considered an early candidate, however the NFL's Chicago Bears objected, citing a possible home game for the 2008 NFL playoffs that weekend (January 3–4); ironically, the Bears ended up being eliminated from contention in the last week. It was decided that the game would be played at Wrigley Field, the North Side home of the Chicago Cubs, as confirmed by the Minneapolis Star-Tribune on July 6. Ten days afterward, the NHL confirmed the reports that the game would officially be held on New Year's Day. Faceoff was scheduled for 1 pm EST (12 noon CST). The Red Wings won the game 6–4.
The NHL and National Hockey League Players' Association (NHLPA) agreed to move the trade deadline from Tuesday, March 3, 2009, to Wednesday, March 4, 2009. This was done mainly because the schedule has twelve games on March 3 and only two on March 4.
General Managers' Meeting
At the meeting, held in Naples, Florida from March 9–11, 2009, general managers of the teams discussed issues that concerned them. Consensus on any topic would lead to action by the Board of Governors or the Competition committee in later meetings. Paul Kelly, executive director of the NHLPA, made a presentation on the topic of dangerous hits to the head, proposing new rules to penalize intentional hits. The general managers could not agree on the planned rule change and took no further action. Kelly intends to review the issue at the future Competition committee meeting, which is held after the Stanley Cup final. The general managers also discussed the topic of fighting in hockey, and agreed to penalize further players who start fights directly after face-offs and to further enforce the existing 'instigator' rule. The managers agreed to award a second-round compensatory pick in the 2009 entry draft to the New York Rangers due to the death of Alexei Cherepanov.