One of the most tumultuous seasons in franchise history, 1999–2000, actually started in July three months prior to the start of the regular season. In the span of a few days, longtime broadcaster Gene Hart died due to illness and defenseman Dmitri Tertyshny, coming off his rookie season, was fatally injured in a freak boating accident. The season itself was no better as head coach Roger Neilson was diagnosed with bone cancer, forcing him to step aside in February 2000 to undergo treatment. The team was left in the hands of interim coach Craig Ramsay for the rest of the season.

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In January, longtime Flyer and fan favorite Rod Brind'Amour was shipped to Carolina for Keith Primeau, with the intention of acquiring a big center to complement Eric Lindros. Meanwhile, the strife between Flyers management (particularly GM Bob Clarke) and Lindros, continued to worsen. Less than a month after Ramsay took over, Lindros suffered his second concussion of the season. He played several games after the initial hit and afterwards criticized the team's training staff for failing to initially diagnose the concussion after it happened. It was after this that the Flyers' organization decided to strip Lindros of the captaincy on March 27 and sew the C on the sweater of defenseman Eric Desjardins. With Lindros out indefinitely, the Flyers rallied to overcome the distractions and a 15-point deficit in the standings to win the Atlantic Division and the No. 1 seed in the East on the last day of the regular season.

They easily defeated their first round opponent, Buffalo, in five games. Primeau's goal in the fifth overtime of Game 4 against the team's second-round opponent, Pittsburgh, turned that series in the Flyers' favor as they won in six games, coming back from a 2–0 series deficit. After dropping Game 1 to New Jersey in the Eastern Conference Finals, the Flyers peeled off three straight wins to take a 3–1 series lead. But New Jersey refused to give up. After New Jersey won Game 5, Lindros returned to the lineup for the first time since March for Game 6 in another losing effort. Early in Game 7, Lindros was on the receiving end of a controversial hit by Scott Stevens, giving him another concussion and leaving the Philadelphia crowd deflated. Without Lindros, the Flyers lost the decisive game by a score of 2–1. It was the 2nd time in franchise history the team lost a series after being up 3 games to 1. To add insult to injury, New Jersey went on to win the Stanley Cup.

The Flyers call the First Union Center their home and have since 1996. The $206 million facility seats more than 21,000 screaming fans for hockey games and also serves as the home to the NBA's 76ers. The arena includes several interactive exhibits and a microbrewery inside. The First Union Center also hosts entertainers such as the Dave Matthews Band, Phish, Billy Joel and Bruce Springsteen.

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