In the 1999 NBA draft, the Raptors acquired Antonio Davis from the Indiana Pacers in exchange of their first round draft pick Jonathan Bender.
Davis provided experience and strong frontcourt presence. Their roster consisting of Vince Carter, Doug Christie, Williams in the backcourt and Williams and Muggsy Bouges for the point guard position and the rotation of Willis, Oakley and Davis in the frontcourt.
As McGrady and Carter had improved, they had led the team to advance to its first ever playoff appearance. Due to a lack of playoff experience, they were swept by the New York Knicks in the first round.
Vince Carter winning the 2000 NBA Slamdunk Contest and his rise to being a superstar has drawn many fans and caught many attention around the league.
They finished the regular season with a 45-37 record, third in the Central Division. They hired Lenny Wilkens as the head coach that has a 30 years of experience and a basketball Hall-of-Famer.
They also signed veteran Mark Jackson. When Alvin Williams has emerged being a clutch player, Jackson was traded and Williams was given more playing time. Vince Carter had filled the shooting guard position allowing the team to trade Christie for Corliss Williamson who turned out to have a disappointing season and later on replaced by Jerome Williams.
They traded McGrady to the Orlando Magic in the 2000 off-season for a first round draft pick. The Raptors advanced through the playoffs and defeated the New York Knicks 3 games to two in the first round. The next round was a showdown of the two best shooting guards in the league. It was entertaining for the fans to see Carter and Allen Iverson colliding.
The Sixers, led by Iverson and Dikembe Mutombo, eliminated the Raptors from the playoffs. They finished the regular season with 47-35, which is the Raptors’ best record, finishing 2nd in the Central Division.
The next season,to ensure that Vince Carter would re-sign with the Raptors, they sign long term contracts with Alvin Williams, Jerome Williams and Antonio Davis.
They also added the former MVP and Superstar center Hakeem Olajuwon to provide Carter a good supporting cast around him. In the season, even though Carter was injured and miss some games including the All-Star game, they managed to qualify for the postseason and faced the Detroit Pistons. They lost against the Pistons in the first round.It was also visible that the Olajuwon experiment was a bust.