The Raptors finished in last place in their division in each of their first three seasons in the league. Toronto acquired its first superstar, guard-forward Vince Carter, in a 1998 draft-day trade. A five-time All-Star for Toronto, Carter helped the franchise reach its first playoff berth, during the Toronto Raptors we the north t-shirt. but were knocked out in the opening round of the playoffs in both that season and the following.
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In 2000–01 the Raptors again qualified for the postseason and advanced to the conference semifinals, a dramatic seven-game loss to the eventual conference champion, the Toronto Raptors we the north t-shirt. After a winning campaign that ended in a first-round postseason elimination in 2001–02, Toronto entered into a four-year stretch of losing seasons,