| Ben Gordon (33) | Tyrus Thomas (9) | Derrick Rose (7) | Philips Arena18,031 | 13–17 |- bgcolor="#bbffbb" | 31 | December 29 | @ New Jersey | | Ben Gordon (24) | Andrés Nocioni (8) | Derrick Rose (13) | Izod Center18,786 | 14–17 |- bgcolor="#ffcccc" | 32 | December 31 | Orlando | | Joakim Noah (19) | Joakim Noah (11) | Thabo Sefolosha, Andrés Nocioni (4) | United Center21,861 | 14–18 |- bgcolor="#ffcccc" | 33 | January 2 | @ Cleveland | | Ben Gordon (22) | Joakim Noah (10) | Ben Gordon (4) | Quicken Loans Arena20,562 | 14–19 |- bgcolor="#ffcccc" | 34 | January 3 | Minnesota | | Derrick Rose (22) | Aaron Gray (9) | Ben Gordon (6) | United Center20,516 | 14–20 |- bgcolor="#bbffbb" | 35 | January 6 | Sacramento | | Ben Gordon (24) | Drew Gooden (10) | Derrick Rose (8) | United Center18,060 | 15–20 |- bgcolor="#bbffbb" | 36 | January 9 | Washington | | Ben Gordon (22) | Drew Gooden (11) | Derrick Rose (9) | United Center20,125 | 16–20 |- bgcolor="#ffcccc" | 37 | January 10 | Oklahoma City | | Ben Gordon (22) | Drew Gooden (12) | Derrick Rose (6) | United Center20,469 | 16–21 |- bgcolor="#ffcccc" | 38 | January 12 | Portland | | Drew Gooden (22) | Drew Gooden (9) | Derrick Rose (10) | United Center18,996 | 16–22 |- bgcolor="#bbffbb" | 39 | January 14 | @ Toronto | | Derrick Rose (25) | Luol Deng (14) | Derrick Rose (10) | Air Canada Centre18,494 | 17–22 |- bgcolor="#bbffbb" | 40 | January 15 | Cleveland | | Luol Deng (22) | Luol Deng (8) | Derrick Rose (6) | United Center21,297 | 18–22 |- bgcolor="#ffcccc" | 41 | January 17 | San Antonio | | Ben Gordon (20) | Andrés Nocioni (15) | Derrick Rose (8) | United Center22,100 | 18–23 |- bgcolor="#ffcccc" | 42 | January 19 | @ New York | | Luol Deng, Derrick Rose (20) | Joakim Noah (18) | Derrick Rose (8) | Madison Square Garden18,807 | 18–24 |- bgcolor="#ffcccc" | 43 | January 20 | Atlanta | | Ben Gordon (21) | Joakim Noah (11) | Kirk Hinrich (8) | United Center20,389 | 18–25 |- bgcolor="#ffcccc" | 44 | January 23 | Toronto | | Ben Gordon (19) | Aaron Gray