| Season | Record | Top Scorer | All-Stars | Postseason |
|---|---|---|---|---|
| 2024-25 | 30-52 (.366) |  RJ Barrett (21.1 ppg) | ||
| 2023-24 | 25-57 (.305) | Pascal Siakam (22.2 ppg) | ||
| 2022-23 | 41-41 (.500) | Pascal Siakam (24.2 ppg) | ||
| 2021-22 | 48-34 (.585) | Pascal Siakam (22.8 ppg) | Eastern Conference First Round: 2-4 | |
| 2020-21 | 27-45 (.375) | Pascal Siakam (21.4 ppg) | ||
| 2019-20 | 53-19 (.736) | Pascal Siakam (22.9 ppg) | Eastern Conference First Round: 4-0 Eastern Conference Semifinals: 3-4 | |
| 2018-19 | 58-24 (.707) | Kawhi Leonard (26.6 ppg) | Eastern Conference First Round: 4-1 Eastern Conference Semifinals: 4-3 Eastern Conference Finals: 4-2 NBA Finals: 4-2 | |
| 2017-18 | 59-23 (.720) | DeMar DeRozan (23 ppg) | Eastern Conference First Round: 4-2 Eastern Conference Semifinals: 0-4 | |
| 2016-17 | 51-31 (.622) | DeMar DeRozan (27.3 ppg) | Eastern Conference First Round: 4-2 Eastern Conference Semifinals: 0-4 | |
| 2015-16 | 56-26 (.683) | DeMar DeRozan (23.5 ppg) | Eastern Conference First Round: 4-3 Eastern Conference Semifinals: 4-3 Eastern Conference Finals: 2-4 | |
| 2014-15 | 49-33 (.598) | DeMar DeRozan (20.1 ppg) | Eastern Conference First Round: 0-4 | |
| 2013-14 | 48-34 (.585) | DeMar DeRozan (22.7 ppg) | Eastern Conference First Round: 3-4 | |
| 2012-13 | 34-48 (.415) | Rudy Gay (19.5 ppg) | ||
| 2011-12 | 23-43 (.348) | Andrea Bargnani (19.5 ppg) | ||
| 2010-11 | 22-60 (.268) | Andrea Bargnani (21.4 ppg) | ||
| 2009-10 | 40-42 (.488) | |||
| 2008-09 | 33-49 (.402) | |||
| 2007-08 | 41-41 (.500) | Eastern Conference First Round: 1-4 | ||
| 2006-07 | 47-35 (.573) | Eastern Conference First Round: 2-4 | ||
| 2005-06 | 27-55 (.329) | |||
| 2004-05 | 33-49 (.402) | Jalen Rose (18.5 ppg) | ||
| 2003-04 | 33-49 (.402) | Vince Carter (22.5 ppg) | ||
| 2002-03 | 24-58 (.293) | Vince Carter (20.6 ppg) | ||
| 2001-02 | 42-40 (.512) | Vince Carter (24.7 ppg) | Eastern Conference First Round: 2-3 | |
| 2000-01 | 47-35 (.573) | Vince Carter (27.6 ppg) | Eastern Conference First Round: 3-2 Eastern Conference Semifinals: 3-4 | |
| 1999-00 | 45-37 (.549) | Vince Carter (25.7 ppg) | Eastern Conference First Round: 0-3 | |
| 1998-99 | 23-27 (.460) | Vince Carter (18.3 ppg) | ||
| 1997-98 | 16-66 (.195) | Damon Stoudamire (19.4 ppg) | ||
| 1996-97 | 30-52 (.366) | Damon Stoudamire (20.2 ppg) | ||
| 1995-96 | 21-61 (.256) | Damon Stoudamire (19 ppg) |