The 2008 WNBA season was the third season in the WNBA for the Chicago Sky. The Sky, were once again, were looking for a new coach after Bo Overton resigned following one season with the Sky. Assistant coach Steven Key was hired as the new head coach and general manager.
The Sky received the second over pick in the 2008 WNBA draft from the draft lottery system. They were able to use this pick on star center Sylvia Fowles out of LSU.
The following player was selected in the Atlanta Dream expansion draft from the Chicago Sky:
|- bgcolor="ffbbbb" | 1 | May 17 | @ Seattle | 61-67 | Chasity Melvin (15) | Candice Dupree (10) | Perkins<br>Price (2) | KeyArena<BR>12,079 | 0-1 |- bgcolor="#bbffbb" | 2 | May 22 | Sacramento | 87-77 | Dupree<br>Price (22) | Sylvia Fowles (7) | Dominique Canty (6) | UIC Pavilion<BR>4,188 | 1-1 |- bgcolor="ffbbbb" | 3 | May 29 | Minnesota | 69-75 | Sylvia Fowles (16) | Sylvia Fowles (11) | Dominique Canty (6) | UIC Pavilion<BR>3,014 | 1-2 |-
|- bgcolor="ffbbbb" | 4 | June 1 | Connecticut | 73-75 | Jia Perkins (21) | Sylvia Fowles (12) | Dominique Canty (5) | UIC Pavilion<BR>2,276 | 1-3 |- bgcolor="ffbbbb" | 5 | June 3 | Los Angeles | 77-81 (OT) | Candice Dupree (22) | Candice Dupree (11) | Dominique Canty (8) | UIC Pavilion<BR>6,304 | 1-4 |- bgcolor="#bbffbb" | 6 | June 6 | @ Atlanta | 86-72 | Canty<BR>Perkins (16) | Dupree<br>Perkins (9) | Price (5) | Philips Arena<BR>7,418 | 2-4 |- bgcolor="#bbffbb" | 7 | June 7 | Atlanta | 91-70 | Candice Dupree (20) | Chasity Melvin (7) | Dominique Canty (6) | UIC Pavilion<BR>3,182 | 3-4 |- bgcolor="ffbbbb" | 8 | June 13 | Washington | 57-64 | Jia Perkins (17) | Candice Dupree (8) | Canty<br>Price (4) | UIC Pavilion<BR>2,600 | 3-5 |- bgcolor="ffbbbb" | 9 | June 18 | @ Los Angeles | 67-80 | Jia Perkins (18) | Candice Dupree (8) | Canty<br>Dupree (3) | STAPLES Center<BR>7,245 | 3-6 |- bgcolor="ffbbbb" | 10 | June 20 | @ Phoenix | 105-112 (OT) | Jia Perkins (30) | Candice Dupree (12) | Candice Dupree (5) | US Airways Center<BR>7,311 | 3-7 |- bgcolor="#ffbbbb" | 11 | June 22 | @ Sacramento | 70-82 | Jia Perkins (22) | Candice Dupree (11) | Dominique Canty (8) | ARCO Arena<BR>6,107 | 3-8 |- bgcolor="#ffbbbb" | 12 | June 26 | Phoenix | 79-89 | Chasity Melvin (19) | Chasity Melvin (15) | Brooke Wyckoff (9) | UIC Pavilion<BR>3,103 | 3-9 |- bgcolor="#bbffbb" | 13 | June 28 | Detroit | 76-59 | Candice Dupree (18) | Dupree<br>Melvin (8) | Chasity Melvin (5) | UIC Pavilion<BR>3,407 | 4-9 |-
|- bgcolor="#bbffbb" | 14 | July 1 | @ Minnesota | 73-71 | Candice Dupree (26) | Chasity Melvin (11) | Dominique Canty (5) | Target Center<BR>4,765 | 5-9 |- bgcolor="#ffbbbb" | 15 | July 2 | @ Indiana | 67-74 | Candice Dupree (20) | Candice Dupree (13) | Dupree<br>Wyckoff (4) | Conseco Fieldhouse<BR>6,196 | 5-10 |- bgcolor="#ffbbbb" | 16 | July 5 | @ Atlanta | 84-91 | Jia Perkins (24) | Candice Dupree (8) | Dominique Canty (6) | Philips Arena<BR>8,468 | 5-11 |- bgcolor="#ffbbbb" | 17 | July 10 | San Antonio | 67-75 | Jia Perkins (17) | Candice Dupree (8) | Canty<br>Perkins (4) | UIC Pavilion<BR>3,040 | 5-12 |- bgcolor="#ffbbbb" | 18 | July 12 | @ Indiana | 57-66 | Candice Dupree (19) | Chasity Melvin (12) | Chasity Melvin (5) | Conseco Fieldhouse<BR>7,134 | 5-13 |- bgcolor="#bbffbb" | 19 | July 13 | Atlanta | 79-66 | Dupree<br>Perkins (18) | Armintie Price (7) | Dupree<br>Perkins<br>Wyckoff<br>Fluker (3) | UIC Pavilion<BR>2,907 | 6-13 |- bgcolor="#ffbbbb" | 20 | July 16 | @ Detroit | 63-66 | Jia Perkins (26) | Candice Dupree (12) | Dupree<br>Melvin (4) | Palace of Auburn Hills<BR>15,210 | 6-14 |- bgcolor="#bbffbb" | 21 | July 18 | Connecticut | 73-65 | Jia Perkins (15) | Candice Dupree (9) | K.B. Sharp (4) | UIC Pavilion<BR>3,379 | 7-14 |- bgcolor="#ffbbbb" | 22 | July 20 | @ Connecticut | 67-74 | Armintie Price (15) | Chasity Melvin (10) | Jia Perkins (5) | Mohegan Sun Arena<BR>7,367 | 7-15 |- bgcolor="#bbffbb" | 23 | July 22 | Indiana | 68-60 | Candice Dupree (20) | Jia Perkins (10) | Jia Perkins (8) | UIC Pavilion<BR>3,035 | 8-15 |- bgcolor="#ffbbbb" | 24 | July 24 | @ San Antonio | 67-78 | Candice Dupree (20) | Candice Dupree (10) | Perkins<br>Sharp (3) | AT&T Center<BR>9,372 | 8-16 |- bgcolor="#ffbbbb" | 25 | July 26 | @ Houston | 65-79 | Candice Dupree (28) | Jia Perkins (7) | Jia Perkins (5) | Reliant Arena<BR>6,569 | 8-17 |-
|- | colspan="10" align="center" valign="middle" | Summer Olympic break |- bgcolor="#bbffbb" | 26 | August 28 | @ New York | 69-60 | Jia Perkins (19) | Sylvia Fowles (10) | Armintie Price (5) | Madison Square Garden<BR>8,566 | 9-17 |- bgcolor="#bbffbb" | 27 | August 29 | @ Washington | 79-75 | Jia Perkins (28) | Sylvia Fowles (13) | Armintie Price (4) | Verizon Center<BR>10,043 | 10-17 |- bgcolor="#bbffbb" | 28 | August 31 | Detroit | 82-81 (OT) | Candice Dupree (24) | Sylvia Fowles (12) | Candice Dupree (7) | UIC Pavilion<BR>4,197 | 11-17 |-
|- bgcolor="#ffbbbb" | 29 | September 4 | Seattle | 62-70 | Jia Perkins (22) | Candice Dupree (6) | Dominique Canty (6) | UIC Pavilion<BR>3,829 | 11-18 |- bgcolor="#ffbbbb" | 30 | September 5 | @ Connecticut | 75-80 | Jia Perkins (18) | Sylvia Fowles (6) | Dominique Canty (7) | Mohegan Sun Arena<BR>8,088 | 11-19 |- bgcolor="#ffbbbb" | 31 | September 7 | @ New York | 61-69 | Jia Perkins (18) | Sylvia Fowles (12) | Canty<br>Sharp (2) | Madison Square Garden<BR>7,903 | 11-20 |- bgcolor="#bbffbb" | 32 | September 9 | Washington | 78-59 | Jia Perkins (17) | Candice Dupree (10) | Candice Dupree (6) | UIC Pavilion<BR>3,087 | 12-20 |- bgcolor="#ffbbbb" | 33 | September 12 | New York | 62-69 | Candice Dupree (18) | Dupree<br>Fowles (6) | Canty<br>Wyckoff (4) | UIC Pavilion<BR>5,681 | 12-21 |- bgcolor="#ffbbbb" | 34 | September 14 | Houston | 76-79 | Candice Dupree (20) | Armintie Price (7) | Dominique Canty (6) | UIC Pavilion<BR>4,917 | 12-22 |-