Perhaps the best two-way season of Recchi's Flyers career came in 1999-2000, as he not only compiled 91 points but also posted a Philadelphia career-best plus-20 rating and, at different junctures played left wing and even center in addition to his preferred right wing position. Recchi placed seventh in the NHL's Hart Trophy balloting and earned his second Bobby Clarke Trophy.
During the latter portion of Recchi's time with the Flyers, he was reunited with his former junior coach Hitchcock. A third Bobby Clarke Trophy followed in 2003-04 as Recchi posted a team-high 75 points in 82 games for a team that adopted a very defensively conscious style of play. Much of the damage was done on the power play, where Recchi racked up 14 goals. In the playoffs, the Flyers fell just one win shy of reaching the Stanley Cup Final.
The year-long NHL lockout of 2004-05 resulted in the cancelation of the season. As an agreement was finally reached between the League and the Players' Association, a salary cap was added to a new Collective Bargaining Agreement (CBA). The Flyers did not retain Recchi and, for cap compliance, bought out the remaining contracts of LeClair and Tony Amonte while trading Jeremy Roenick to the Los Angeles Kings in order to accommodate the free agent signing of superstar center Peter Forsberg.
Recchi remained in the NHL for an additional six seasons following the end of his second stint with the Flyers. He earned a second Stanley Cup ring as a member of the 2005-06 Carolina Hurricanes, contributing 16 points (seven goals and nine assists) in 25 playoff games during the team's run to the championship. His final 20-plus goal season came at age 38, when he posted 24 goals and 68 points while dressing in every game of the 2006-07 season; the first year of Recchi's one-plus-season third stint with the Penguins.
Recchi's NHL playing career ended gloriously. In 2010-11, as a member of the Boston Bruins, he lifted the Stanley Cup for the third and final time, and contributed 14 points (five goals, nine assists) during the 25-game run. The 43-year-old player, who set an NHL record as the oldest player to score a goal in the Stanley Cup Final, retired after the season.
After his playing days, Recchi served as a consultant to the Dallas Stars and then became a player development coach for the Pittsburgh Penguins.