1998/99: A year after taking talented high school star Tracy McGrady in the draft the Raptors select his cousin Vince Carter who was a star at UNC. However, Toronto fans would have to wait to see the talented cousins in action as a 4-month lockout delayed the start of the season. When the season started the Raptors new arena was almost ready, as they beat the Vancouver Grizzlies 102-87 in their first game at the Air Canada Centre on February 21st. After years of playing in the spacious SkyDome the Raptors finally had an arena built for basketball and they clearly benefited as they finally escaped last place by posting a record of 23-27. Leading the promising Raptors was Vince Carter who became the 2nd Raptor in 4 years to win Rookie of the Year with 18.3 ppg. At season's end Carter took the microphone and addressed the ACC crowd after the final game and guaranteed a trip to the post-season next year.

1999/00: With the off-season acquisition of Antonio Davis for a high draft pick, the Raptors not only got older, they got a whole lot better. As Davis along with Charles Oakley who was acquired a year earlier provided veteran stability to a young talented team. The veteran presence helped make Vince Carter into an All-Star as he received the second most amount of all star votes ever while stealing the show in the Slam Dunk Contest which he won easily. Carter would go on to average a team high 25.7 ppg while his cousin Tracy McGrady finished second with 15.4 ppg, as the Raptors fulfilled Vince Carter's guarantee with a 45-37 record. However, in the playoffs the inexperienced Raptors would be schooled by the playoff tested New York Knicks losing in 3 straight games. Following the season, the Raptors would be jilted by Tracy McGrady, who decided to seek his own fame, out of his cousin's shadow by signing with the Orlando Magic.

2000/01: After their first playoff appearance the Raptors decided to go after a Hall of Fame coach, to lead the team to the next step as the hired al-time winingest Coach Lenny Wilkins. Vince Carter continued to establish himself as the next big star in the NBA by leading the Raptors with an impressive 27.6 pp, after exhibiting show-stopping dunks in the Olympics with Team USA. With the continued improvement of Vince Carter the Raptors would finish in 2nd place with a solid record of 47-35. In the playoffs the Raptors were matched up against the New York Knicks for the second year in a row. After splitting the first 2 games in New York the Raptors appeared to be heading for a disappointing exit again after they lost Game 3 at the ACC 97-89. However, the Raptors would send the series back to New York by winning Game 4 100-93. In the decisive 5th game in New York the Raptors would stun the Knicks 93-89 to advance to the 2nd round. In the 2nd round the Raptors were matched up against the top seed Philadelphia 76ers. However the Raptors would give the 7ers all they could handle as the battled tooth and nailed all the way to a 7th game where Vince Carter missed a buzzer beater with the Raptors down 88-87, which would have sent the Raptors on the Eastern Conference Finals.

2001/02: After experience success in the playoffs the Raptors were able to sign Vince Carter to a long-term multimillion-dollar deal to ensure their marquee stars for years to come. In addition the Raptors would add even more star power by acquiring future Hall of Famer Hakeem Olajuwon from the Houston Rockets. The Raptors appeared to be heading for another strong season as they held a record of 29-21 entering the all-star break. However, in the final game before the break Vince Carter suffered a knee injury that would hamper their star for the rest of the season. In the second half the Raptors lost 18 of 19 games including, 13 straight games following the break. With all hopes of the playoff seemingly lost Vince Carter decided to undergo knee surgery. However, the Raptors would suddenly turn thing around as they won 8 straight without Vince Carter to get back into the playoff picture. The Raptors would do on to slip into the playoff as the 7th seed with a record of 42-40. In the playoffs the Raptors would get off to a shaky start as they dropped the first 2 games on the road to the Detroit Pistons. However, coming home the Raptors would rebound nicely winning 2 games at ACC to force a decisive 5th game. In Game 5 at Detroit the Raptors gave the Pistons all they could handle before losing 85-82.

2002/03: Things looked bleak for the Raptors early in the season as Hakeem Olajuwon announced his retirement following a disappointing first season in Toronto. In addition Vince Carter continued to feel the lingering effect of his knee injury as he missed most of the first half. However, some former teammates and NBA observes began to question Carter's heart and desire and he didn't seem to be a hurry to get back in the lineup. This view was even given further ammo when Carter was dancing on stage with Nelly as the Raptors, were getting blown out by the Hawks in Atlanta. The Raptors would have all hopes for the playoff buried in January as they held a record of 8-28, which included a 12-game losing streak. Vince Carter would return and play most of the second half, averaging 20.6 ppg, but the Raptors struggles continues as Coach Lenny Wilkins who already held the record for most career wins set the record for most career losses as a coach, while the Raptors finished in 7th place with a disappointing record of 24-58. Following the final game GM Glenn Grunwald apologized to the fans at ACC announcing changes would be made. He would get started right away by firing Coach Lenny Wilkins.

2003/04: With new Coach Kevin O'Neill the Raptors started the season on a high note beating the 2-time Eastern Conference Champion New Jersey Nets 90-87. However a few days later they would set an embarrassing post shot clock record by scoring just 56 points in a loss to the Minnesota Timberwolves. That kind of inconsistency would become the hallmark of the Raptors all season, at times they looked like genuine playoff contenders, while others they looked like a last place team. At 8-8 the Raptors pulled off a blockbuster deal with the Chicago Bulls on December 1st acquiring Jalen Rose, Donyell Marshall, and Lonny Baxter in exchange for Antonio Davis, Jerome Williams, and Chris Jefferies. The Raptors would win their first 3 games after the deal but won just 1 of 7 following the initially strong start as the Raptors continued through out the entire first half as they sat at 25-25 at the All Star Break. However after the all star break injuries would become a problem as the Raptors won just 8 games the rest of the way finishing with a 33-49 record. Following the season the Raptors would fire Coach O'Neill choosing to go with Sam Mitchell.

2004/05: The Sam Mitchell era got off to a good start as the Raptors won 4 of their first 5 games. However the joy was short lived as the Raptors came back to earth fast, as a disgruntled Vince Carter continued to sulk, which hit rock bottom in a November 12th loss in Seattle as he told the Supersonics what play the team was going to run in the waning moments of an 88-87 loss. Through December the Raptors struggled badly winning just 3 of 15 games, as they finally gave up on Vince Carter as he was traded to the New Jersey Nets for Eric Williams, Aaron Williams, Alonzo Mourning, and two first-round draft picks. Mourning a future Hall of Famer refused to play for the Raptors and forced a buyout as he returned to the Miami Heat where he had his best years. Meanwhile the Raptors would go to finish tied for last place in the Atlantic Division with a 33-49 record, while Chris Bosh started to emerge as the new star of the Toronto with a solid 16.8 ppg and 8.9 rpg in just his second year.

2005/06: Under new Coach Sam Mitchell not much was expected from the Raptors who were clearly in a rebuilding mindset as they were still feeling the effects of the Vince Carter deal, in which they got nothing substantial in return, while many questioned their decision to draft Charlie Villanueva. When the season start the Raptors were struggling to match even their low expectations as they lost 15 of their first 16 games. In December the Raptors would show some improvement as they split 14 games as Chris Bosh put together an All-Star season leading the Raptors with 22.5 ppg. The Raptors would continue to play .500 ball in an up and down January that saw them set a franchise record for points in a game while a week later they were torched by Kobe Bryant for 81 points. January would also see changes in Management as GM Mike Babcock was fired and eventually replaced by Bryan Colangelo. The Raptors would close the season much as they begun losing 12 of their last 13, with Chris Bosh injured as they finished in 4th Place with a 27-55 record. The Raptors poor record would have one beneficial side effect as they won the top pick in the draft lottery which they used on Italian prodigy Andrea Bargnani, making him the first European drafted number one overall. While they would trade Charlie Villanueva, who would prove critics wrong by finishing second in Rookie of the Year Voting to the Milwaukee Bucks for play making Point Guard T.J. Ford.