Primeau became a leader with his new team when the franchise moved to North Carolina and became the Carolina Hurricanes, being named team captain in 1998–99. However, he missed the majority of the 1999–2000 NHL season after holding out and was traded to the Philadelphia Flyers (along with a 2000 fifth-round draft pick, ultimately used to select Kristofer Ottosson) in exchange for Rod Brind'Amour, Jean-Marc Pelletier and a 2000 second-round draft pick (Agris Saviels) on January 23, 2000. On May 5, 2000, Primeau scored the game-winning goal in the longest game in modern NHL playoff history (five overtime periods for a total of 152 minutes and one second) against Ron Tugnutt of the Pittsburgh Penguins in Game 4 of the Eastern Conference Semifinals. Only two games, in 1933 and 1936, were longer.