2008–09 Portland Trail Blazers season Game log January

| Game | Date_ | Team | Score | High_points | High_rebounds | High_assists | Location_Attendance | Record |
|---|---|---|---|---|---|---|---|---|
| 38 | January 14 | @ Philadelphia | L 79–100 (OT) | Brandon Roy (27) | LaMarcus Aldridge , Joel Przybilla (9) | Brandon Roy (6) | Wachovia Center 14,561 | 23–15 |
| 39 | January 15 | @ New Jersey | W 105–99 (OT) | Brandon Roy (29) | Joel Przybilla (11) | Brandon Roy (5) | Izod Center 13,824 | 24–15 |
| 40 | January 17 | @ Charlotte | L 97–102 (OT) | LaMarcus Aldridge (21) | Joel Przybilla (10) | Brandon Roy (6) | Time Warner Cable Arena 17,482 | 24–16 |
| 41 | January 19 | Milwaukee | W 102–85 (OT) | Greg Oden (24) | Greg Oden (15) | Sergio Rodríguez , Brandon Roy (7) | Rose Garden 20,580 | 25–16 |
| 42 | January 21 | Cleveland | L 98–104 (OT) | Brandon Roy (23) | Joel Przybilla (15) | Sergio Rodríguez (5) | Rose Garden 20,632 | 25–17 |