Roster
| No. | Player | Pos | Ht | Wt | Birth Date | Exp | College |
| 14 | Muggsy Bogues | PG | 5-3 | 136 | January 9, 1965 | 12 | Wake Forest University |
| 7 | Dee Brown | PG | 6-1 | 160 | November 29, 1968 | 9 | Jacksonville University |
| 15 | Vince Carter | SF | 6-6 | 215 | January 26, 1977 | 1 | University of North Carolina |
| 13 | Doug Christie | SG | 6-6 | 200 | May 9, 1970 | 7 | Pepperdine University |
| 30 | Dell Curry | SG | 6-4 | 190 | June 25, 1964 | 13 | Virginia Polytechnic |
| 33 | Antonio Davis | C | 6-9 | 215 | October 31, 1968 | 6 | University of Texas at El Paso |
| 21 | Antonio Lang | SF | 6-8 | 205 | May 15, 1972 | 5 | Duke University |
| 22 | Sean Marks | PF | 6-10 | 250 | August 23, 1975 | 1 | University of California |
| 1 | Tracy McGrady | SF | 6-8 | 210 | May 24, 1979 | 2 | none |
| 34 | Charles Oakley | PF | 6-8 | 225 | December 18, 1963 | 14 | Virginia Union University |
| 25 | Aleksandar Radojevic | C | 7-3 | 250 | August 8, 1976 | R | Barton County Community College |
| 4 | Michael Stewart | C | 6-10 | 230 | April 25, 1975 | 2 | University of California |
| 12 | John Thomas | C | 6-9 | 265 | September 8, 1975 | 2 | University of Minnesota |
| 20 | Alvin Williams | PG | 6-5 | 185 | August 6, 1974 | 2 | Villanova University |
| 42 | Kevin Willis | PF | 7-0 | 220 | September 6, 1962 | 14 | Michigan State University |
| 3 | Haywoode Workman | PG | 6-2 | 180 | January 23, 1966 | 7 | Oral Roberts University |
Transactions
-June 30/99: With the 5th pick of the NBA draft (obtained from Denver), the Raptors selected Jonathan Bender from Picayune High School in Mississippi. A 6-11 centre who averaged 23.1 ppg, 15 rpg and 5 blocks and 4 assists in his senior high school year. With the 12th pick of the draft, the Raptors select Aleksandar Radojevic, a Yugoslavian-born centre from Barton County CC in Kansas. Grunwald says he’s a talented player “who has a very bright future ahead of him. But he is a project and he’s going to be a long-term project.”
-July 1/99: Charles Oakley, Paul Rogers, Reggie Slater, Michael Stewart, Negele Knight, John Wallace and Michael Williams become free agents.
-July 1/99: Trade Jonathan Bender to Indiana for 6-11 journeyman forward Antonio Davis, (drafted by the Pacers in the second round of the 1990 draft). The trade is finalized August 1st.
-August 1/99: Release Michael Williams.
-August 5/99: Sign free agent Dell Curry (from Milwaukee) to a multi-year contract.
-August 12/99: Sign Michael Stewart to a multi-year contract.
-August 31/99: Release free agents Negele Knight, Paul Rogers and Reggie Slater.
-September 2/99: Sign Charles Oakley to a multi-year contract.
-September 22/99: Sign free agent Muggsy Bogues (from Charlotte).
-October 4/99: Sign Antonio Lang as a free agent. Sign Alek Radojevic to a multi-year contract.
-October 7/99: Sign Kevin Willis to a veteran extension of his contract.
-October 27/99: Waive Antonio Lang.
-January 14/00: Sign Antonio Lang to the first of a pair of 10-day contracts.
-February 9/00: Trade Alvin Williams and Sean Marks to the Boston Celtics for Danny Fortson. The trade is voided two days later. Claim Haywoode Workman on waivers from Milwaukee Bucks.
Standings
| Eastern Conference | W | L | W/L% | GB | PS/G | PA/G |
| Atlantic Division | ||||||
| Miami Heat | 52 | 30 | .634 | — | 94.4 | 91.3 |
| New York Knicks | 50 | 32 | .610 | 2.0 | 92.1 | 90.7 |
| Philadelphia 76ers | 49 | 33 | .598 | 3.0 | 94.8 | 93.4 |
| Orlando Magic | 41 | 41 | .500 | 11.0 | 100.1 | 99.4 |
| Boston Celtics | 35 | 47 | .427 | 17.0 | 99.3 | 100.1 |
| New Jersey Nets | 31 | 51 | .378 | 21.0 | 98.0 | 99.0 |
| Washington Wizards | 29 | 53 | .354 | 23.0 | 96.6 | 99.9 |
| Central Division | ||||||
| Indiana Pacers | 56 | 26 | .683 | — | 101.3 | 96.7 |
| Charlotte Hornets | 49 | 33 | .598 | 7.0 | 98.4 | 95.8 |
| Toronto Raptors | 45 | 37 | .549 | 11.0 | 97.2 | 97.3 |
| Detroit Pistons | 42 | 40 | .512 | 14.0 | 103.5 | 102.0 |
| Milwaukee Bucks | 42 | 40 | .512 | 14.0 | 101.2 | 101.0 |
| Cleveland Cavaliers | 32 | 50 | .390 | 24.0 | 97.0 | 100.5 |
| Atlanta Hawks | 28 | 54 | .341 | 28.0 | 94.3 | 99.7 |
| Chicago Bulls | 17 | 65 | .207 | 39.0 | 84.8 | 94.2 |
| Western Conference | W | L | W/L% | GB | PS/G | PA/G |
| Midwest Division | ||||||
| Utah Jazz | 55 | 27 | .671 | — | 96.5 | 92.0 |
| San Antonio Spurs | 53 | 29 | .646 | 2.0 | 96.2 | 90.2 |
| Minnesota Timberwolves | 50 | 32 | .610 | 5.0 | 98.5 | 96.0 |
| Dallas Mavericks | 40 | 42 | .488 | 15.0 | 101.4 | 102.0 |
| Denver Nuggets | 35 | 47 | .427 | 20.0 | 99.0 | 101.1 |
| Houston Rockets | 34 | 48 | .415 | 21.0 | 99.5 | 100.3 |
| Vancouver Grizzlies | 22 | 60 | .268 | 33.0 | 93.9 | 99.5 |
| Pacific Division | ||||||
| Los Angeles Lakers | 67 | 15 | .817 | — | 100.8 | 92.3 |
| Portland Trail Blazers | 59 | 23 | .720 | 8.0 | 97.5 | 91.0 |
| Phoenix Suns | 53 | 29 | .646 | 14.0 | 98.9 | 93.7 |
| Seattle SuperSonics | 45 | 37 | .549 | 22.0 | 99.1 | 98.1 |
| Sacramento Kings | 44 | 38 | .537 | 23.0 | 105.0 | 102.0 |
| Golden State Warriors | 19 | 63 | .232 | 48.0 | 95.5 | 103.8 |
| Los Angeles Clippers | 15 | 67 | .183 | 52.0 | 92.0 | 103.5 |
Playoffs
| Eastern Conference First Round (3-0): | New York Knickerbockers over Toronto Raptors |
| Game 1 April 23 Toronto Raptors 88 @ New York Knickerbockers 92 Game 2 April 26 Toronto Raptors 83 @ New York Knickerbockers 84 Game 3 April 30 New York Knickerbockers 87 @ Toronto Raptors 80 |
Raptors 1999-2000 Player Stats at basketballreference.com
Salaries
| 1 | Charles Oakley | $5,236,000 |
| 2 | Antonio Davis | $4,200,000 |
| 3 | Dee Brown | $4,000,000 |
| 4 | Michael Stewart | $3,200,000 |
| 5 | Doug Christie | $2,742,600 |
| 6 | Kevin Willis | $2,625,000 |
| 7 | Vince Carter | $2,267,280 |
| 8 | Dell Curry | $2,100,000 |
| 9 | Alvin Williams | $1,925,000 |
| 10 | Tracy McGrady | $1,767,120 |
| 11 | B.J. Tyler | $1,614,000 |
| 12 | Aleksandar Radojevic | $1,325,760 |
| 13 | John Thomas | $832,560 |
| 14 | Muggsy Bogues | $510,000 |
| 15 | Sean Marks | $385,000 |
Season wrap
General manager Glen Grunwald, searching for leadership and maturity, trades draft pick Jonathan Bender to forward Antonio Davis. The Raptors can’t seem to settle on a point guard but the frontcourt leads them to their first playoff appearance, where they are swept in the opening round by the New York Knicks. The Raptors play their first full season at the Air Canada Centre, setting attendance records (17,568), while finishing 45-37 on the campaign. During the playoffs, coach Butch Carter speaks about a lack of leadership in the dressing room. Just before playoffs, Carter filed a $5-million lawsuit against former Raptor Marcus Camby, who called Carter a “liar” in a New York newspaper story for having once assured him that Camby was to be the cornerstone of the Raptors team two years ago. Shortly thereafter, Camby was traded to the Knicks for Charles Oakley. The move was condemned by the league. Carter withdrew the suit and the Knicks swept the Raptors. Carter also made a play for Glen Grunwald’s general manager job and later dropped the lawsuit. “It was difficult with all that was going on to stay focused on basketball,” veteran guard Doug Christie said. Other veterans, such as Antonio Davis and Charles Oakley said the season was marred by the jump-shooting excesses of Carter and McGrady. After the season, the Raptors turf Carter and replace him with legendary coach Lenny Wilkins. Vince Carter is chosen a third team NBA all-star, the first Raptor to be named to the all-star game and wins the slam dunk contest on all-star weekend. Free agent Tracy McGrady, appearing disgruntled that he wasn’t getting top billing over Carter, bails for the Orlando Magic and US$67.5 million/six years in a sign-and-trade deal that gives the Raptors a first round draft pick, while giving up a conditional draft pick.