Crosby became the league's all-time leader in assists for a single franchise after registering his 1,112th assist for Pittsburgh. He later scored to draw level with Marcel Dionne for sixth place on the NHL's all-time points list, with 1,771.
However, his individual achievements were not enough to prevent the Penguins from suffering defeat as Montreal secured its fifth consecutive victory.
Josh Anderson scored twice for the Canadiens, while Chris Kreider, Oliver Kapanen and Alexandre Texier also found the net. Jacob Fowler made 25 saves to help Montreal extend its impressive run.
McDavid extends remarkable scoring streak
Connor McDavid continued his outstanding start to the campaign as the Edmonton Oilers recorded a convincing 4-0 victory over the New York Islanders.
Ryan Nugent-Hopkins scored twice, while Vasily Podkolzin and Jason Dickinson added the other goals. McDavid registered an assist to extend his season-opening point streak to 14 games, taking his assist tally to a league-leading 29.
Goaltender Tristan Jarry also delivered an impressive performance, stopping all 18 shots to record his second consecutive shutout.
Bruins complete dramatic comeback against Blackhawks
The Boston Bruins recovered from a two-goal deficit in the third period to defeat the Chicago Blackhawks 5-4 in overtime.
Chicago appeared to be in control after Ryan Greene and Connor Bedard scored consecutive goals to establish a 4-2 advantage.
However, Mason Lohrei reduced the deficit before Morgan Geekie scored with just 12 seconds remaining to force overtime.
Elias Lindholm then completed the comeback by scoring the winning goal in extra time. Chicago finished with 41 shots on goal but could not secure the victory.
Stamkos inspires Predators against Lightning
Steven Stamkos returned to haunt his former team as the Nashville Predators defeated the Tampa Bay Lightning 5-4 in a shootout.
Stamkos scored a third-period power-play goal to send the contest into overtime before converting the decisive attempt in the shootout.
Nikita Kucherov registered three assists for Tampa Bay, but his contribution could not prevent the Lightning from suffering defeat.
Blues edge Red Wings in another 5-4 thriller
The St. Louis Blues defeated the Detroit Red Wings 5-4 in a closely contested encounter.
Detroit fought back after falling behind early, scoring three consecutive goals to take control of the contest. However, the Blues responded with a strong attacking display.
Justin Barron levelled the score at 4-4 before Aleksanteri Kaskimaki scored just 18 seconds later to hand St. Louis the victory.
The Blues managed only 15 shots on goal compared with Detroit's 28, making their efficiency in front of goal particularly significant.
Senators overpower Sharks
The Ottawa Senators produced a commanding performance to defeat the San Jose Sharks 5-1.
After San Jose drew level at 1-1, Ottawa scored four unanswered goals to take control of the game.
Drake Batherson and Tim Stützle both scored their ninth goals of the season, while Dylan Cozens and Shane Pinto each contributed a goal and an assist.
Ottawa also dominated the shooting statistics, registering 35 shots compared with San Jose's 23.
Sabres defeat Kings as Thompson scores twice
The Buffalo Sabres secured a 3-2 victory over the Los Angeles Kings, with Tage Thompson scoring twice.
Buffalo found the net once in each period, while goaltender Ukko-Pekka Luukkonen made 27 saves to help his team claim a third consecutive victory.
The result extended Los Angeles' difficult run, with the Kings continuing to struggle for goals.
Maple Leafs overcome Canucks
The Toronto Maple Leafs defeated the Vancouver Canucks 4-2 after scoring three of the final four goals in the contest.
Auston Matthews scored his 11th goal of the season to extend his opening road point streak to eight games, while William Nylander also found the net with his 10th goal of the campaign.
Brock Boeser and Max Sasson scored for Vancouver, but Toronto held on to secure the victory.
Stars defeat Blue Jackets
The Dallas Stars recorded a 3-1 win over the Columbus Blue Jackets, with Mikko Rantanen, Thomas Harley and Arttu Hyry scoring.
Rantanen opened the scoring with a power-play goal, while Harley doubled Dallas' advantage just before the end of the first period.
Damon Severson pulled one back for Columbus in the third period, but Hyry sealed the victory with an empty-net goal.
Jake Oettinger made 25 saves for Dallas.
Other scheduled fixture
The Halloween programme also included the Calgary Flames' visit to the Colorado Avalanche. The game was still in progress when the Flashscore roundup was updated.
NHL results – Saturday, 31 October 2026
• Montreal Canadiens: 5-4 Pittsburgh Penguins
• Edmonton Oilers: 4-0 New York Islanders
• Boston Bruins: 5-4 Chicago Blackhawks (OT)
• Nashville Predators: 5-4 Tampa Bay Lightning (SO)
• St. Louis Blues: 5-4 Detroit Red Wings
• Ottawa Senators: 5-1 San Jose Sharks
• Buffalo Sabres: 3-2 Los Angeles Kings
• Toronto Maple Leafs: 4-2 Vancouver Canucks
• Dallas Stars: 3-1 Columbus Blue Jackets
The Halloween fixtures delivered several dramatic finishes, but Crosby's historic milestones and McDavid's continued scoring consistency stood out as two of the biggest talking points from the NHL action.