18 April 2009 April 2009 | Miami FC (USA) (2) | 3 - 1 | Cleveland City Stars (11) |
25 April 2009 April 2009 | Austin Aztex FC (USA) (3) | 3 - 0 | Cleveland City Stars (11) |
1 Mei 2009 Mei 2009 | Cleveland City Stars (10) | 0 - 3 | Rochester New York FC (USA) (4) |
9 Mei 2009 Mei 2009 | Cleveland City Stars (10) | 0 - 0 | Portland Timbers (USA) (3) |
16 Mei 2009 Mei 2009 | Minnesota Thunder (USA) (11) | 0 - 1 | Cleveland City Stars (10) |
22 Mei 2009 Mei 2009 | Cleveland City Stars (10) | 0 - 3 | North Carolina FC (USA) (1) |
29 Mei 2009 Mei 2009 | North Carolina FC (USA) (1) | 1 - 0 | Cleveland City Stars (10) |
30 Mei 2009 Mei 2009 | Charleston Battery (USA) (2) | 2 - 0 | Cleveland City Stars (10) |
4 Juni 2009 Juni 2009 | Puerto Rico Islanders (PUR) (1) | 2 - 1 | Cleveland City Stars (10) |
6 Juni 2009 Juni 2009 | Puerto Rico Islanders (PUR) (1) | 2 - 2 | Cleveland City Stars (10) |
13 Juni 2009 Juni 2009 | Cleveland City Stars (10) | 3 - 0 | Rochester New York FC (USA) (5) |
18 Juni 2009 Juni 2009 | Cleveland City Stars (10) | 1 - 2 | Miami FC (USA) (7) |
20 Juni 2009 Juni 2009 | Cleveland City Stars (10) | 0 - 1 | Miami FC (USA) (7) |
23 Juni 2009 Juni 2009 | Cleveland City Stars (10) | 2 - 2 | Vancouver Whitecaps (CAN) (8) |
27 Juni 2009 Juni 2009 | Cleveland City Stars (10) | 2 - 2 | Austin Aztex FC (USA) (9) |
3 Juli 2009 Juli 2009 | Cleveland City Stars (11) | 0 - 1 | Austin Aztex FC (USA) (9) |
12 Juli 2009 Juli 2009 | Cleveland City Stars (11) | 0 - 0 | Puerto Rico Islanders (PUR) (3) |
17 Juli 2009 Juli 2009 | Cleveland City Stars (11) | 0 - 0 | Charleston Battery (USA) (1) |
22 Juli 2009 Juli 2009 | CF Montréal (CAN) (8) | 4 - 1 | Cleveland City Stars (11) |
25 Juli 2009 Juli 2009 | Rochester New York FC (USA) (5) | 4 - 1 | Cleveland City Stars (11) |
1 Augustus 2009 Augustus 2009 | Cleveland City Stars (11) | 0 - 0 | Vancouver Whitecaps (CAN) (7) |
8 Augustus 2009 Augustus 2009 | North Carolina FC (USA) (2) | 2 - 0 | Cleveland City Stars (11) |
11 Augustus 2009 Augustus 2009 | Charleston Battery (USA) (3) | 4 - 1 | Cleveland City Stars (11) |
18 Augustus 2009 Augustus 2009 | Cleveland City Stars (11) | 1 - 2 | CF Montréal (CAN) (6) |
22 Augustus 2009 Augustus 2009 | Cleveland City Stars (11) | 1 - 0 | Minnesota Thunder (USA) (9) |
27 Augustus 2009 Augustus 2009 | Minnesota Thunder (USA) (9) | 3 - 0 | Cleveland City Stars (11) |
5 September 2009 September 2009 | Cleveland City Stars (11) | 1 - 2 | CF Montréal (CAN) (6) |
13 September 2009 September 2009 | Portland Timbers (USA) (1) | 0 - 1 | Cleveland City Stars (11) |
17 September 2009 September 2009 | Portland Timbers (USA) (1) | 2 - 1 | Cleveland City Stars (11) |
18 September 2009 September 2009 | Vancouver Whitecaps (CAN) (7) | 2 - 1 | Cleveland City Stars (11) |