The 1999–2000 NBA season was the 53rd season of the National Basketball Association in New York City. During the offseason, the Knicks re-signed free agent John Wallace. In his second year with the Knicks, Latrell Sprewell became a starter after playing off the bench last season and averaged 18.6 points per game. After advancing to the NBA Finals as the #8 seed last year, the Knicks finished second in the Atlantic Division with a 50–32 record, good enough for their first 50-win season since 1997. Allan Houston was selected to play in the 2000 NBA All-Star Game. In the first round of the playoffs, the Knicks swept the Toronto Raptors in three straight games. In the semifinals, they faced the Miami Heat for the fourth consecutive year. They would defeat the 2nd-seeded Heat in a tough hard fought seven game series, but would lose in six games to the Indiana Pacers in the Eastern Conference Finals.

This season marked an end of an era as Patrick Ewing was traded to the Seattle SuperSonics following the season. Also following the season, Chris Dudley was traded to the Phoenix Suns, and Wallace was traded to the Dallas Mavericks, who then traded him to the Detroit Pistons.

(3) New York Knicks vs. (6) Toronto Raptors Last Playoff Meeting: This is the first playoff meeting between the Raptors and Knicks.

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