2008–09 Cleveland Cavaliers season Game log January

| Game | Date_ | Team | Score | High_points | High_assists | Location_Attendance | Record |
|---|---|---|---|---|---|---|---|
| 37 | January 15 | @ Chicago | L 93–102 (OT) | LeBron James (28) | LeBron James (7) | United Center 21,297 | 30–7 |
| 38 | January 16 | New Orleans | W 92–78 (OT) | LeBron James (29) | LeBron James (7) | Quicken Loans Arena 20,562 | 31–7 |
| 39 | January 19 | @ L.A. Lakers | L 88–105 (OT) | LeBron James (23) | Maurice Williams (5) | Staples Center 18,997 | 31–8 |
| 40 | January 21 | @ Portland | W 104–98 (OT) | LeBron James (34) | LeBron James (14) | Rose Garden 20,632 | 32–8 |
| 41 | January 23 | @ Golden State | W 106–105 (OT) | LeBron James (32) | LeBron James (8) | Oracle Arena 19,596 | 33–8 |
| 42 | January 24 | @ Utah | W 102–97 (OT) | LeBron James (33) | LeBron James (9) | EnergySolutions Arena 19,911 | 34–8 |