1999–2000 Toronto Raptors season Game log January

| Game | Date_ | Team | Score | High_points | High_rebounds | High_assists | Location_Attendance | Record |
|---|---|---|---|---|---|---|---|---|
| 39 | January 19 | @ Boston | L 90–94 (OT) | Vince Carter (20) | Charles Oakley (10) | Muggsy Bogues , Alvin Williams (5) | FleetCenter 16,124 | 20-19 |
| 40 | January 23 | Seattle | W 94–77 (OT) | Antonio Davis , Tracy McGrady (17) | Kevin Willis (12) | Doug Christie (6) | Air Canada Centre 19,800 | 21-19 |
| 41 | January 26 | Washington | W 120–105 (OT) | Vince Carter (26) | Kevin Willis (9) | Charles Oakley (8) | Air Canada Centre 17,582 | 22-19 |
| 42 | January 28 | Miami | W 108–93 (OT) | Vince Carter (23) | Antonio Davis (12) | Charles Oakley (7) | Air Canada Centre 19,800 | 23-19 |