| 05/02/2010 2:00 PM | Challengers | Naper Wolves | Commissioners Park | TitansCC | | Challengers Won Challengers:162/5 in 25.0 Wolves:51/8 in 25.0 |  |
| 05/16/2010 2:00 PM | Challengers | Chicago Titans | Commissioners Park | CenturionsCC | | Chicago Titans Won Challengers:125/10 in 25.0 Titans:126/4 in 18.3 | |
| 05/23/2010 9:00 AM | Centurions | Challengers | Commissioners Park | Greater ChicagoCricket Academy | | Centurions Won Centurions:188/6 in 25.0 Challengers:126/8 in 25.0 | |
| 06/05/2010 9:00 AM | Greater Chicago Cricket Association | Challengers | Commissioners Park | CardinalsCC | | Greater Chicago Cricket Association Won GCCA:172/7 in 25.0 Challengers:122/10 in 23.0 | |
| 06/06/2010 9:00 AM | Greater Chicago Cricket Association | Challengers | Commissioners Park | | | Greater Chicago Cricket Association Won GCCA:175/7 in 25.0 Challengers:118/10 in 22.0 | |
| 06/12/2010 2:00 PM | Cardinals | Challengers | Commissioners Park | FriendsCC | | Match Tied Cardinals:0/0 in 0.0 Challengers:0/0 in 0.0 | |
| 06/26/2010 9:00 AM | Challengers | Friends | Commissioners Park | | | Friends Won Challengers:137/10 in 23.0 Friends:138/4 in 20.0 | |
| 07/10/2010 2:00 PM | Spartans | Challengers | Commissioners Park | | | | |
| 07/17/2010 9:00 AM | Challengers | KCC Knights | Commissioners Park | | | Challengers Won Challengers:166/10 in 24.4 KCC:134/8 in 25.0 | |
| 07/25/2010 9:00 AM | Challengers | Naper Wolves | Commissioners Park | | | Naper Wolves Won Challengers:157/7 in 25.0 Wolves:158/1 in 15.0 | |
| 08/01/2010 1:30 PM | Challengers | Chicago Titans | Commissioners Park | | | Chicago Titans Won Challengers:159/8 in 25.0 Titans:161/5 in 18.4 | |
| 08/07/2010 2:00 PM | Centurions | Challengers | Commissioners Park | | | Centurions Won Centurions:153/9 in 25.0 Challengers:98/10 in 25.0 | |
| 08/14/2010 9:00 AM | KCC Knights | Challengers | Commissioners Park | | | Challengers Won KCC:138/7 in 25.0 Challengers:139/7 in 22.0 | |