His record-breaking 916th will come against the Tampa Bay Lightning at Amalie Arena (7 p.m. ET; NHLN, SUN, ATTSN-PT, NHL.TV).
There have been numerous memorable moments in Crosby's 14 seasons with the Penguins, who selected him No. 1 in the 2005 NHL Draft in Ottawa. Here are 14 of the most memorable in chronological order:
Editor's Note: These do not include Crosby's achievements with Canada.
Crosby scored his first NHL goal in his first home game at the since-demolished Mellon Arena in Pittsburgh on Oct. 8, 2005. It was his third NHL game.
Crosby scored on the power play at 18:32 of the second period to give the Penguins a 6-4 lead against the Boston Bruins. The goal came 6:48 after Lemieux scored to make it 5-4. Mark Recchi and Zigmund Palffy had the assists. The Penguins lost 7-6 in overtime.
Video: BOS@PIT: Crosby collects rebound for first NHL goal
First six-point game
Crosby scored six points (one goal, five assists), which remains his NHL single-game high, in an 8-4 win against the Philadelphia Flyers on Dec. 13, 2006. He matched that total with two goals and four assists in a 6-4 win against the New York Islanders on Jan. 19, 2010.
Against the Flyers, Crosby scored at 5:06 of the first period and had assists on goals by Sergei Gonchar, Ryan Malone, Gonchar again, Recchi and Michel Ouellet.
First game-winning playoff goal
Crosby's scored the first of nine game-winning Stanley Cup Playoff goals in his career April 14, 2007. It was the second of his 66 playoff goals. The goal came at 11:44 of the third period during a 4-3 win at the Ottawa Senators in Game 2 of the Eastern Conference Quarterfinals.
Crosby scored in his first playoff game three nights earlier with 49 seconds remaining in a 6-3 loss.
Following Lemieux as captain
The Penguins named Crosby their first captain since Lemieux on May 31, 2007.
Lemieux retired after playing 26 games in the 2005-06 season. Pittsburgh played the rest of that season and all of 2006-07 season without a captain.
Crosby was named captain more than two months before his 20th birthday (Aug. 7). At 19 years, 297 days old, he surpassed Lightning center Vincent Lecavalier as the youngest full-time captain in NHL history by 27 days.
That title now belongs to center Connor McDavid, who was named Edmonton Oilers captain on Oct. 5, 2016, when he was 19 years, 266 days old.
Crosby won the Hart Trophy as NHL MVP for the first time June 14, 2007.
He finished the 2006-07 season with an NHL-high 120 points (36 goals, 84 assists) in 79 games, becoming the youngest player to win the Art Ross Trophy as the League scoring leader and the only teenager in the history of the four major professional sports leagues to win a scoring title.
Crosby won the Hart and Art Ross again in 2013-14 when he had 104 points (36 goals, 68 assists) in 80 games.
Shootout in Buffalo blizzard
Crosby's first major moment on national television in the United States took place during a blizzard in Buffalo. He scored the shootout winner to give the Penguins a 2-1 win against the Buffalo Sabres in the first NHL Winter Classic at Ralph Wilson Stadium on Jan. 1, 2008.
He pushed the puck ahead through the snow that had piled up on the ice, fooled Ryan Miller with a backhand-forehand deke and stuffed the puck into the net between Miller's legs. The call from Mike "Doc" Emrick on NBC is iconic.
"The game on his stick right here. … Score! Penguins win!"
Video: 2008 Winter Classic: Sidney Crosby's SO game-winner
Dueling hat tricks
Crosby's link with Washington Capitals left wing Alex Ovechkin grew tighter on May 4, 2009, when the two faces of the NHL played each other in Game 2 of the Eastern Conference Semifinals.
Each scored a hat trick in the Capitals' 4-3 win in Washington. It is arguably the most iconic head-to-head moment between Crosby and Ovechkin.
Video: Memories: Ovechkin and Crosby record hat tricks
First Stanley Cup championship
One year and eight days after watching the Detroit Red Wings celebrate a Stanley Cup championship in Pittsburgh, Crosby and the Penguins turned the tables in Detroit. They won Game 7 of the 2009 Stanley Cup Final 2-1 at Joe Louis Arena on June 12, 2009.
Crosby wasn't able to play for most of the final two periods. He was injured on a check from Johan Franzen at 5:30 in the second period. He didn't play again in the period and took one shift in the third.
It didn't stop him from joining his teammates in the postgame celebration on the ice. At 21, he became the youngest player to receive the Stanley Cup from NHL Commissioner Gary Bettman.
Returning in style
Crosby was out more than 10 months because of problems related to a concussion he sustained in 2010-11. He didn't miss a beat when he got back and made his season debut Nov. 21, 2011, 320 days after playing his last game of 2010-11.
Crosby had two goals and two assists in a 5-0 home win against the New York Islanders. He scored on his third shift, then had an assist on his fifth.
Second championship, plus more
Crosby celebrated the seven-year anniversary of his first Stanley Cup championship by winning the Cup again June 12, 2016. He had two assists in a 3-1 win against the San Jose Sharks 3-1 in Game 6 of the Stanley Cup Final at SAP Center.
Crosby also won the Conn Smythe Trophy as playoff MVP for the first time. He had 19 points (six goals, 13 assists) in 24 playoff games.
Video: PIT@SJS, Gm6: Crosby receives Conn Smythe Trophy
Crosby joined Lemieux and Jaromir Jagr as the only players in NHL history to score 1,000 points with the Penguins. He reached the mark with an assist on Chris Kunitz's first-period goal in a 4-3 win against the Winnipeg Jets on Feb. 16, 2017. He did it in his 757th NHL game, making him the 12th-fastest player in NHL history to reach 1,000 points.
Crosby has since passed Jagr to move into second on the Penguins scoring list with 1,177 points (434 goals, 743 assists). Lemieux is first with 1,723 points (690 goals, 1,033 assists). Jagr had 1,079 points (439 goals, 640 assists) in 806 games.
Video: WPG@PIT: Crosby sets up Kunitz for 1,000th point
Game 5 at Nashville
Crosby's best game during the Penguins' run to their second straight Stanley Cup championship was arguably Game 5 of the Stanley Cup Final at home against the Nashville Predators at PPG Paints Arena on June 8, 2017. The 6-0 win gave Pittsburgh a 3-2 lead in the best-of-7 series.
Crosby had three assists and generally could not be stopped. He opened the game by turning a 1-on-2 into a breakaway that led to a Predators penalty, which led to Crosby setting up Penguins defenseman Justin Schultz for a power-play goal at 1:31 of the first period.
He also assisted on second-period goals by Conor Sheary (1:19) and Phil Kessel (8:02).
Third championship, second Conn Smythe Trophy
Three nights after his vintage performance in Game 5, Crosby helped the Penguins to a Cup-clinching 2-0 win at Bridgestone Arena in Nashville. The Penguins became the first team since the 1997-98 Detroit Red Wings to repeat as Stanley Cup champions.
Crosby won the Conn Smythe Trophy again. He finished the playoffs with 27 points (eight goals, 19 assists) in 24 games.
Video: PIT@NSH, Gm6: Crosby speaks about third Stanley Cup
All-Star Game MVP
Crosby overcame a stomach flu that prevented him from participating in the first two days of 2019 Honda NHL All-Star Weekend to win the online fan voting for MVP of the 2019 Honda NHL All-Star Game at SAP Center in San Jose on Jan. 26.
Crosby scored eight points (four goals, four assists) to help the Metropolitan Division win the All-Star Game. He had three points (two goals, one assist) in the Metropolitan's 7-4 win against the Atlantic Division in the second semifinal game, and five points (two goals, three assists) in a 10-5 win against the Central Division in the final.
He was one of four finalists fans could vote for and received 49 percent of the vote. The NHL gave him a 2019 Honda Passport Elite for winning MVP honors.
Video: MET@CEN: Crosby crowned 2019 NHL All-Star MVP