The 1999–2000 Pittsburgh Penguins season was the team's 33rd in the National Hockey League. It was the first season under ownership led by former superstar Mario Lemieux.

Off-season

In June 1999, a U.S. Bankruptcy Court Judge granted former player Mario Lemieux ownership of the Penguins franchise, who were in danger of either relocating to Portland, Oregon, or folding. Lemieux received final approval of team ownership by NHL Commissioner Gary Bettman on September 3, 1999.

Regular season

On April 7, 2000, Jaromir Jagr scored just 13 seconds into the overtime period to give the Penguins a 2–1 road win over the Buffalo Sabres. It would prove to be the fastest overtime goal scored during the 1999–2000 regular season.

Final standings

Schedule and results

Regular season

Playoffs

Player statistics

†Denotes player spent time with another team before joining the Penguins. Stats reflect time with the Penguins only. ‡Denotes player was traded mid-season. Stats reflect time with the Penguins only.

Awards and records

Awards

Milestones

Transactions

The Penguins have been involved in the following transactions during the 1999–2000 season:

Trades

Free agents acquired

Free agents lost

Claimed via waivers

Player signings

Other

Draft picks

Pittsburgh Penguins' picks at the 1999 NHL Entry Draft.

Farm teams

The Wilkes-Barre/Scranton Penguins, previously known as the Cornwall Aces, debuted in the AHL as the top minor league affiliate for the Pittsburgh Penguins. Playing in the Empire State Division, they finished last overall in the Western Conference with a record of 23-43-9-5. WBRE, the NBC station in Wilkes-Barre/Scranton, received a James H. Ellery Memorial Award for outstanding television coverage. Marketing executives Brian Magness and Rich Hixon won the Ken McKenzie Award as the league's outstanding marketing executives. The Wheeling Nailers of the East Coast Hockey League finished the season in fifth place in the Northwest Division with a record of 25-40-5.