2008 Chicago Sky season Regular season September

| Game | Date_ | Opponent | Score | High_points | High_rebounds | High_assists | Location_Attendance | Record |
|---|---|---|---|---|---|---|---|---|
| 29 | September 4 | Seattle | 62-70 | Perkins (22) | Dupree (6) | Canty (6) | UIC Pavilion 3,829 | 11-18 |
| 30 | September 5 | @ Connecticut | 75-80 | Perkins (18) | Fowles (6) | Canty (7) | Mohegan Sun Arena 8,088 | 11-19 |
| 31 | September 7 | @ New York | 61-69 | Perkins (18) | Fowles (12) | Canty , Sharp (2) | Madison Square Garden 7,903 | 11-20 |
| 32 | September 9 | Washington | 78-59 | Perkins (17) | Dupree (10) | Dupree (6) | UIC Pavilion 3,087 | 12-20 |
| 33 | September 12 | New York | 62-69 | Dupree (18) | Dupree , Fowles (6) | Canty , Wyckoff (4) | UIC Pavilion 5,681 | 12-21 |