On Monday, the Pittsburgh Penguins announced they extended their captain Sidney Crosby with a two-year agreement. The top pick from the 2005 Draft will begin his 20th season with the franchise on Oct. 9.

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Besides being the longest-tenured leader in Penguins history, Crosby sits behind Hall of Famer Mario Lemieux in goals, assists, and points. With a possible 264 games left in his career, Sid the Kid had a chance to chase down his mentor and become Pittsburgh’s greatest statistical player.

On the cusp of 600 goals, we thought it would be fun to revisit all his milestone goals from one to 500 to celebrate his contract announcement.

Related: BREAKING: Crosby signs two-year contract extension

Here’s a refresher for those who have forgotten the dates, goalies, and opponents.

First Goal (Oct. 8, 2005)

Hannu Toivonen (Boston Bruins) at Mellon Arena

Crosby began his career with points in his first six games, picking up assists in his first two games. Even though the Penguins had started the season 0-4-5, the 18-year-old Crosby had 12 points in those nine games.

In his third game, he collected his NHL goal on the power play at 18:32 of the second period against Hannu Toivonen and the Boston Bruins at Mellon Arena. Hall of Famer Mark Recchi and Ziggy Palffy set up his first lamplight.

Crosby would finish the night with three points (two assists), while the Bruins would spoil the evening’s festive atmosphere by winning in overtime, 7-6

Related: 7 Fascinating Statistics About Sidney Crosby’s Career

Fun fact: This goal was the only time Crosby beat Toivonen in his career.

100th Goal (Oct. 18, 2008)

Curtis Joseph (Toronto Maple Leafs) at Mellon Arena

In his 218th NHL game, Crosby scored his 100th goal at 12:15 of the third period to help the Penguins defeat the Toronto Maple Leafs 4-1. He contributed to every goal in the contest, earning three assists for his 10th four-point game.

His milestone lamplighter came against Curtis Joseph and was an even-strength marker assisted by Evgeni Malkin and Kris Letang. This goal was the only one Crosby would tally on Joseph.

Fun fact: Joseph surrendered eight 100th goals during his career, including players like Recchi, Tomas Holmstrom, and Henrik Zetterberg.

200th Goal (Nov. 27, 2010)

Miikka Kiprusoff (Calgary Flames) at CONSOL Energy Center

Pittsburgh fans didn’t have to wait as long for Crosby to tally his next milestone goal, registering his 200th lamplighter just two years later on Nov. 27, 2010.

In another home contest, this time against Miikka Kuprusoff and the Calgary Flames, Crosby collected his seventh career hat trick, powering the Penguins to a 3-0 victory.

His second tally of the night came on the power play at 9:12 of the third period. Assists on the milestone goal came from Paul Martin and Kris Letang. Crosby would add a shorthanded empty net goal for the icing on the cake to complete the hat trick.

Related: Analyzing Crosby’s Chance at 2,000 Points

Fun fact: Kiprusoff would give up four goals to Crosby over his career. Meanwhile, David Legwand and Martin Havlat also collected their 200th goal against the Finnish netminder.

300th Goal (Apr. 1, 2015)

Steve Mason (Philadelphia Flyers) at CONSOL Energy Center

Considering Crosby has collected 129 career points against his Pennsylvania rival, the Philadelphia Flyers, everybody knows they would eventually appear on a milestone list.

As Crosby continued climbing the Penguins’ all-time goal-scoring list, he tallied his team’s only lamplighter in a 4-1 loss to Steve Mason and the Flyers on Apr. 1, 2015. Opening the scoring in the first period, at 3:29, he buried his 300th goal thanks to assists from Patric Hornqvist and Ian Cole.

Fun fact: Mason gave up seven goals to Crosby, with six coming in a Flyers uniform from 2013 to 2016.

400th Goal (Feb. 11, 2018)

Jake Allen (St. Louis Blues) at Scottrade Center

Crosby has scored some memorable goals in his career, but when he became only the third Penguins skater to reach 400 goals, he achieved the milestone on the road.

In the second period of a game against the St. Louis Blues, Crosby tied the contest at 1-1 with his even-strength goal at 3:31 on netminder Jake Allen. The single assist went to Conor Sheary. Pittsburgh would win 4-1, with the captain collecting an empty net goal in the third period.

Related: Contract Extension Would Allow Crosby to Chase Rarely Discussed NHL Record

Fun fact: Eric Staal also scored his 400th goal against Allen, achieving his milestone goal on Nov. 3, 2018.

500th Goal (Feb. 15, 2022)

Carter Hart (Philadelphia Flyers) at PPG Paints Arena

The Flyers appear on the list again, this time surrendering Crosby’s 500th career goal on Jaromir Jagr‘s 50th birthday on Feb. 15, 2022. In the first period of a 5-4 Penguins overtime victory, the captain gave the home team a 2-1 lead with his power play tally against Carter Hart at 16:34.

Malkin picked up the only assist on the milestone goal, while Crosby would finish the evening with two points after setting up Jake Guentzel‘s goal in the third period.

Fun fact: Crosby has scored at least three goals against the remaining 31 teams in the NHL but has a career-high 55 lamplighters against the Flyers.

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