| Season | Record | Top Scorer | All-Stars | Postseason |
|---|---|---|---|---|
| 2023-24 | 39-43 (.476) |  DeMar DeRozan (24.0 ppg) | ||
| 2022-23 | 40-42 (.488) | DeMar DeRozan | ||
| 2021-22 | 46-36 (.561) | DeMar DeRozan (27.9 ppg) | DeMar DeRozan | Eastern Conference First Round: 1-4 |
| 2020-21 | 31-41 (.431) | |||
| 2019-20 | 22-43 (.338) | |||
| 2018-19 | 22-60 (.268) | |||
| 2017-18 | 27-55 (.329) | Nikola Mirotić (16.8 ppg) | ||
| 2016-17 | 41-41 (.500) | Eastern Conference First Round: 2-4 | ||
| 2015-16 | 42-40 (.512) | Pau Gasol | ||
| 2014-15 | 50-32 (.610) | Pau Gasol | Eastern Conference First Round: 4-2 Eastern Conference Semifinals: 2-4 | |
| 2013-14 | 48-34 (.585) | Luol Deng (19 ppg) | Joakim Noah | Eastern Conference First Round: 1-4 |
| 2012-13 | 45-37 (.549) | Luol Deng (16.5 ppg) | Luol Deng Joakim Noah | Eastern Conference First Round: 4-3 Eastern Conference Semifinals: 1-4 |
| 2011-12 | 50-16 (.758) | Luol Deng | Eastern Conference First Round: 2-4 | |
| 2010-11 | 62-20 (.756) | Eastern Conference First Round: 4-1 Eastern Conference Semifinals: 4-2 Eastern Conference Finals: 1-4 | ||
| 2009-10 | 41-41 (.500) | Eastern Conference First Round: 1-4 | ||
| 2008-09 | 41-41 (.500) | Ben Gordon (20.7 ppg) | Eastern Conference First Round: 3-4 | |
| 2007-08 | 33-49 (.402) | Ben Gordon (18.6 ppg) | ||
| 2006-07 | 49-33 (.598) | Ben Gordon (21.4 ppg) | Eastern Conference First Round: 4-0 Eastern Conference Semifinals: 2-4 | |
| 2005-06 | 41-41 (.500) | Ben Gordon (16.9 ppg) | Eastern Conference First Round: 2-4 | |
| 2004-05 | 47-35 (.573) | Eddy Curry (16.1 ppg) | Eastern Conference First Round: 2-4 | |
| 2003-04 | 23-59 (.280) | Jamal Crawford (17.3 ppg) | ||
| 2002-03 | 30-52 (.366) | Jalen Rose (22.1 ppg) | ||
| 2001-02 | 21-61 (.256) | Jalen Rose (23.8 ppg) | ||
| 2000-01 | 15-67 (.183) | Elton Brand (20.1 ppg) | ||
| 1999-00 | 17-65 (.207) | Elton Brand (20.1 ppg) | ||
| 1998-99 | 13-37 (.260) | Toni Kukoč (18.8 ppg) | ||
| 1997-98 | 62-20 (.756) | Eastern Conference First Round: 3-0 Eastern Conference Semifinals: 4-1 Eastern Conference Finals: 4-3 NBA Finals: 4-2 | ||
| 1996-97 | 69-13 (.841) | Eastern Conference First Round: 3-0 Eastern Conference Semifinals: 4-1 Eastern Conference Finals: 4-1 NBA Finals: 4-2 | ||
| 1995-96 | 72-10 (.878) | Eastern Conference First Round: 3-0 Eastern Conference Semifinals: 4-1 Eastern Conference Finals: 4-0 NBA Finals: 4-2 | ||
| 1994-95 | 47-35 (.573) | Eastern Conference First Round: 3-1 Eastern Conference Semifinals: 2-4 | ||
| 1993-94 | 55-27 (.671) | B.J. Armstrong Horace Grant | Eastern Conference First Round: 3-0 Eastern Conference Semifinals: 3-4 | |
| 1992-93 | 57-25 (.695) | Eastern Conference First Round: 3-0 Eastern Conference Semifinals: 4-0 Eastern Conference Finals: 4-2 NBA Finals: 4-2 | ||
| 1991-92 | 67-15 (.817) | Eastern Conference First Round: 3-0 Eastern Conference Semifinals: 4-3 Eastern Conference Finals: 4-2 NBA Finals: 4-2 | ||
| 1990-91 | 61-21 (.744) | Eastern Conference First Round: 3-0 Eastern Conference Semifinals: 4-1 Eastern Conference Finals: 4-0 NBA Finals: 4-1 | ||
| 1989-90 | 55-27 (.671) | Eastern Conference First Round: 3-1 Eastern Conference Semifinals: 4-1 Eastern Conference Finals: 3-4 | ||
| 1988-89 | 47-35 (.573) | Eastern Conference First Round: 3-2 Eastern Conference Semifinals: 4-2 Eastern Conference Finals: 2-4 | ||
| 1987-88 | 50-32 (.610) | Eastern Conference First Round: 3-2 Eastern Conference Semifinals: 1-4 | ||
| 1986-87 | 40-42 (.488) | |||
| 1985-86 | 30-52 (.366) | |||
| 1984-85 | 38-44 (.463) | Eastern Conference First Round: 1-3 | ||
| 1983-84 | 27-55 (.329) | Orlando Woolridge (19.3 ppg) | ||
| 1982-83 | 28-54 (.341) | Reggie Theus (23.8 ppg) | Reggie Theus | |
| 1981-82 | 34-48 (.415) | Artis Gilmore (18.5 ppg) | Artis Gilmore | |
| 1980-81 | 45-37 (.549) | Reggie Theus (18.9 ppg) | Artis Gilmore Reggie Theus | Eastern Conference First Round: 2-0 Eastern Conference Semifinals: 0-4 |
| 1979-80 | 30-52 (.366) | Reggie Theus (20.2 ppg) | ||
| 1978-79 | 31-51 (.378) | Artis Gilmore (23.7 ppg) | Artis Gilmore | |
| 1977-78 | 40-42 (.488) | Artis Gilmore (22.9 ppg) | Artis Gilmore | |
| 1976-77 | 44-38 (.537) | Artis Gilmore (18.6 ppg) | Norm Van Lier | Eastern Conference First Round: 1-2 |
| 1975-76 | 24-58 (.293) | Bob Love (19.1 ppg) | Norm Van Lier | |
| 1974-75 | 47-35 (.573) | Bob Love (22 ppg) | Eastern Conference Semifinals: 4-2 Eastern Conference Finals: 3-4 | |
| 1973-74 | 54-28 (.659) | Bob Love (21.8 ppg) | Chet Walker Norm Van Lier | Eastern Conference Semifinals: 4-3 Eastern Conference Finals: 0-4 |
| 1972-73 | 51-31 (.622) | Bob Love (23.1 ppg) | Bob Love Chet Walker | Eastern Conference Semifinals: 3-4 |
| 1971-72 | 57-25 (.695) | Bob Love (25.8 ppg) | Bob Love | Eastern Conference Semifinals: 0-4 |
| 1970-71 | 51-31 (.622) | Bob Love (25.2 ppg) | Chet Walker Bob Love | Eastern Conference Semifinals: 3-4 |
| 1969-70 | 39-43 (.476) | Chet Walker (21.5 ppg) | Chet Walker | Division Semifinals: 1-4 |
| 1968-69 | 33-49 (.402) | Bob Boozer (21.7 ppg) | Jerry Sloan | |
| 1967-68 | 29-53 (.354) | Bob Boozer (21.5 ppg) | Bob Boozer | Division Semifinals: 1-4 |
| 1966-67 | 33-48 (.407) | Guy Rodgers (18.7 ppg) | Guy Rodgers Jerry Sloan | Division Semifinals: 0-3 |
