| 28 May 1939 | Illinois Cricket Association League 1939 | | Chicago Cricket Club v Lake Shore |
| 30 May 1939 | Illinois Cricket Association League 1939 | | Lake Shore v South Park |
| 04 Jun 1939 | Illinois Cricket Association League 1939 | | Chicago Cricket Club v Hyde Park |
| 18 Jun 1939 | Illinois Cricket Association League 1939 | | Lake Shore v River Forest |
| 25 Jun 1939 | Illinois Cricket Association League 1939 | | Lake Shore v Winnetka |
| 04 Jul 1939 | Illinois Cricket Association League 1939 | | Chicago Cricket Club v Lake Forest |
| 09 Jul 1939 | Illinois Cricket Association League 1939 | | Chicago Cricket Club v Washington Park |
| 23 Jul 1939 | Illinois Cricket Association League 1939 | | Chicago Cricket Club v South Park |
| 30 Jul 1939 | Illinois Cricket Association League 1939 | | Lake Shore v Oak Park |
| 06 Aug 1939 | Illinois Cricket Association League 1939 | | Chicago Cricket Club v Lake Shore |
| 13 Aug 1939 | Illinois Cricket Association League 1939 | | Chicago Cricket Club v Oak Park |
| 13 Aug 1939 | Illinois Cricket Association League 1939 | | Chicago Cricket Club v Oak Park |
| 13 Aug 1939 | Illinois Cricket Association League 1939 | | Hyde Park v Lake Forest |
| 27 Aug 1939 | Illinois Cricket Association League 1939 | | Chicago Cricket Club v Milwaukee |
| 27 Aug 1939 | Illinois Cricket Association League 1939 | | Washington Park v Oak Park |
| 10 Sep 1939 | Illinois Cricket Association League 1939 | | Chicago Cricket Club v River Forest |
| 10 Sep 1939 | Illinois Cricket Association League 1939 | | Oak Park v South Park |
| 17 Sep 1939 | Illinois Cricket Association League 1939 | | Lake Shore v Lake Forest |
| 17 Sep 1939 | Illinois Cricket Association League 1939 | | Washington Park v Chicago Cricket Club |
| 24 Sep 1939 | Illinois Cricket Association League 1939 | | Lake Shore v Washington Park |
| 08 Oct 1939 | Illinois Cricket Association League 1939 | | Hyde Park v Lake Shore |
| 14 May 1939 | Illinois Cricket Association League 1939 | | Lake Shore v Hyde Park |
| 15 Oct 1939 | Illinois Cricket Association League 1939 | | Chicago Cricket Club v Winnetka |
| 08 Oct 1939 | Illinois Cricket Association League 1939 | Challenge Match | Chicago Cricket Club v Rest of Illinois |
| 30 May 1939 | Century of Progress Knockout Tournament 1939 | Bye Round | Oak Park v Chicago Cricket Club |
| 11 Jun 1939 | Century of Progress Knockout Tournament 1939 | First Round | Lake Shore v South Park |
| 19 Aug 1939 | Other matches in United States of America 1939 | | Chicago and Oak Park v Old Timers |
| 02 Jul 1939 | Other matches in United States of America 1939 | | Illinois v Missouri |
| 17 Jul 1938 | Illinois Cricket Association League 1938 | | Lake Shore v Chicago Cricket Club |
| 24 Jul 1938 | Illinois Cricket Association League 1938 | | Chicago Cricket Club v Winnetka |
| 31 Jul 1938 | Illinois Cricket Association League 1938 | | Chicago Cricket Club v Washington Park |
| 31 Jul 1938 | Illinois Cricket Association League 1938 | | Lake Shore v Lake Forest |
| 07 Aug 1938 | Illinois Cricket Association League 1938 | | Chicago Cricket Club v Melbourne |
| 07 Aug 1938 | Illinois Cricket Association League 1938 | | Lake Shore v Winnetka |
| 14 Aug 1938 | Illinois Cricket Association League 1938 | | Oak Park v Winnetka |
| 21 Aug 1938 | Illinois Cricket Association League 1938 | | Lake Shore v River Forest |
| 02 Oct 1938 | Illinois Cricket Association League 1938 | | Winnetka v Lake Forest |
| 02 Oct 1938 | Illinois Cricket Association League 1938 | | Lake Shore v Washington Park |
| 09 Oct 1938 | Illinois Cricket Association League 1938 | Challenge Match | Rest of Illinois v Winnetka |
| 17 Sep 1938 | Century of Progress Knockout Tournament 1938 | First Round | Chicago Cricket Club v Melbourne |
| 11 Sep 1938 | Century of Progress Knockout Tournament 1938 | First Round | Lake Shore v Hyde Park |
| 16 Oct 1938 | Century of Progress Knockout Tournament 1938 | Semi-Final | Winnetka v Lake Forest |
| 23 Oct 1938 | Century of Progress Knockout Tournament 1938 | Final | Chicago Cricket Club v Winnetka |
| 03 Jul 1938 | Chicago Cricket Gymkhana 1938 | | Chicago v Buffalo and St Catharines |
| 03 Jul 1938 | Chicago Cricket Gymkhana 1938 | | Winnetka and Lake Shore v Missouri |
| 04 Jul 1938 | Chicago Cricket Gymkhana 1938 | | Chicago v Michigan |
| 06 Jul 1938 | Chicago Cricket Gymkhana 1938 | | Winnetka and Lake Shore v Buffalo and St Catharines |
| 07 Jul 1938 | Chicago Cricket Gymkhana 1938 | | KA Auty's XI v Buffalo and St Catharines |
| 07 Jul 1938 | Chicago Cricket Gymkhana 1938 | | Philadelphia v Winnipeg St George's |
| 08 Jul 1938 | Chicago Cricket Gymkhana 1938 | | Chicago v Winnipeg St George's |
| 08 Jul 1938 | Chicago Cricket Gymkhana 1938 | | Washington Park and Hyde Park v Nondescripts |
| 09 Jul 1938 | Chicago Cricket Gymkhana 1938 | | Chicago v Nondescripts |
| 09 Jul 1938 | Chicago Cricket Gymkhana 1938 | | Illinois v Winnipeg St George's |
| 11 Jul 1938 | Chicago Cricket Gymkhana 1938 | | DW Catling's XI v Winnipeg St George's |
| 30 Jul 1938 | Other matches in United States of America 1938 | | Illinois Cricket Association Juniors v DW Catling's XI |
| 13 Aug 1938 | Other matches in United States of America 1938 | | Illinois Cricket Association Juniors v DW Catling's XI |
| 19 Sep 1938 | Other matches in United States of America 1938 | | Illinois Cricket Association Juniors v DW Catling's XI |
| 06 Aug 1938 | Other matches in United States of America 1938 | | Chicago v Old Timers |
| 02 Jul 1938 | Chicago Cricket Gymkhana 1938 | | Chicago v Missouri |
| 12 May 1940 | Illinois Cricket Association League 1940 | | Lake Shore v River Forest |
| 19 May 1940 | Illinois Cricket Association League 1940 | | Chicago Cricket Club v Lake Shore |
| 26 May 1940 | Illinois Cricket Association League 1940 | | Lake Shore v Milwaukee |
| 30 May 1940 | Illinois Cricket Association League 1940 | | Chicago Cricket Club v Hyde Park |
| 02 Jun 1940 | Illinois Cricket Association League 1940 | | Lake Shore v Winnetka |
| 09 Jun 1940 | Illinois Cricket Association League 1940 | | Chicago Cricket Club v Oak Park |
| 16 Jun 1940 | Illinois Cricket Association League 1940 | | Lake Shore v South Park |
| 23 Jun 1940 | Illinois Cricket Association League 1940 | | Chicago Cricket Club v Washington Park |
| 30 Jun 1940 | Illinois Cricket Association League 1940 | | Chicago Cricket Club v South Park |
| 04 Jul 1940 | Illinois Cricket Association League 1940 | | Chicago Cricket Club v Lake Forest |
| 14 Jul 1940 | Illinois Cricket Association League 1940 | | Lake Shore v Chicago Cricket Club |
| 28 Jul 1940 | Illinois Cricket Association League 1940 | | Lake Shore v Lake Forest |
| 04 Aug 1940 | Illinois Cricket Association League 1940 | | Chicago Cricket Club v Winnetka |
| 04 Aug 1940 | Illinois Cricket Association League 1940 | | Chicago Cricket Club v River Forest |
| 11 Aug 1940 | Illinois Cricket Association League 1940 | | Lake Shore v Hyde Park |
| 25 Aug 1940 | Illinois Cricket Association League 1940 | | Lake Shore v Oak Park |
| 08 Sep 1940 | Illinois Cricket Association League 1940 | | Lake Shore v Washington Park |
| 22 Sep 1940 | Illinois Cricket Association League 1940 | | Chicago Cricket Club v Milwaukee |
| 29 Sep 1940 | Illinois Cricket Association League 1940 | | Chicago Cricket Club v Washington Park |
| 06 Oct 1940 | Illinois Cricket Association League 1940 | Play-off | Lake Forest v Winnetka |
| 13 Oct 1940 | Illinois Cricket Association League 1940 | Challenge Match | Rest of Illinois v Winnetka |
| 30 May 1940 | Century of Progress Knockout Tournament 1940 | Bye Round | Chicago Cricket Club v Hyde Park |
| 07 Jul 1940 | Century of Progress Knockout Tournament 1940 | First Round | Lake Shore v Oak Park |
| 25 Aug 1940 | Century of Progress Knockout Tournament 1940 | First Round | Lake Shore v Oak Park |
| 22 Sep 1940 | Century of Progress Knockout Tournament 1940 | Final | Lake Forest v Winnetka |
| 06 Jul 1940 | Other matches in United States of America 1940 | | Illinois v Detroit West Indians |
| 05 Jul 1940 | Other matches in United States of America 1940 | | KA Auty's XI v Michigan |
| 07 Jul 1940 | Other matches in United States of America 1940 | | Illinois v Michigan |
| 30 May 1941 | Illinois Cricket Association League 1941 | | Chicago Cricket Club v Lake Forest |
| 01 Jun 1941 | Illinois Cricket Association League 1941 | | Lake Shore v Chicago Cricket Club |
| 08 Jun 1941 | Illinois Cricket Association League 1941 | | Lake Shore v Winnetka |
| 15 Jun 1941 | Illinois Cricket Association League 1941 | | Chicago Cricket Club v Washington Park |
| 22 Jun 1941 | Illinois Cricket Association League 1941 | | Lake Shore v Oak Park |
| 04 Jul 1941 | Illinois Cricket Association League 1941 | | Chicago Cricket Club v Oak Park |
| 06 Jul 1941 | Illinois Cricket Association League 1941 | | Lake Shore v Washington Park |
| 20 Jul 1941 | Illinois Cricket Association League 1941 | | Lake Shore v South Park |
| 03 Aug 1941 | Illinois Cricket Association League 1941 | | Chicago Cricket Club v South Park |
| 03 Aug 1941 | Illinois Cricket Association League 1941 | | Lake Shore v Hyde Park |
| 17 Aug 1941 | Illinois Cricket Association League 1941 | | Chicago Cricket Club v Lake Shore |
| 24 Aug 1941 | Illinois Cricket Association League 1941 | | Chicago Cricket Club v Milwaukee |
| 31 Aug 1941 | Illinois Cricket Association League 1941 | | Lake Shore v Lake Forest |
| 01 Sep 1941 | Illinois Cricket Association League 1941 | | Chicago Cricket Club v Winnetka |
| 07 Sep 1941 | Illinois Cricket Association League 1941 | | Chicago Cricket Club v Hyde Park |
| 05 Oct 1941 | Illinois Cricket Association League 1941 | Challenge Match | Rest of Illinois v Winnetka |
| 13 Jul 1941 | Century of Progress Knockout Tournament 1941 | First Round | Chicago Cricket Club v Oak Park |
| 13 Jul 1941 | Century of Progress Knockout Tournament 1941 | First Round | Lake Shore v Lake Forest |
| 14 Sep 1941 | Century of Progress Knockout Tournament 1941 | Semi-Final | Chicago Cricket Club v Winnetka |
| 14 Sep 1941 | Century of Progress Knockout Tournament 1941 | Semi-Final | Lake Shore v Washington Park |
| 21 Sep 1941 | Century of Progress Knockout Tournament 1941 | Final | Washington Park v Winnetka |
| 05 Jul 1941 | Other matches in United States of America 1941 | | Illinois v Michigan |
| 06 Jul 1941 | Other matches in United States of America 1941 | | KA Auty's XI v Michigan |
| 24 May 1942 | Illinois Cricket Association League 1942 | | Chicago Cricket Club v Hyde Park |
| 31 May 1942 | Illinois Cricket Association League 1942 | | Chicago Cricket Club v South Park |
| 14 Jun 1942 | Illinois Cricket Association League 1942 | | Chicago Cricket Club v Oak Park |
| 28 Jun 1942 | Illinois Cricket Association League 1942 | | Chicago Cricket Club v Lake Forest |
| 23 Aug 1942 | Illinois Cricket Association League 1942 | | Chicago Cricket Club v Winnetka |
| 30 Nov 1941 | Illinois Cricket Association League 1942 | | Chicago Cricket Club v Milwaukee |
| 04 Oct 1942 | Century of Progress Knockout Tournament 1942 | Final | Chicago Cricket Club v Hyde Park |
| 31 May 1943 | Illinois Cricket Association League 1943 | | South Park v Winnetka |
| 06 Jun 1943 | Illinois Cricket Association League 1943 | | Chicago Cricket Club v Oak Park |
| 04 Jul 1943 | Illinois Cricket Association League 1943 | | Chicago Cricket Club v Winnetka and Oak Park |
| 05 Jul 1943 | Illinois Cricket Association League 1943 | | Chicago Cricket Club v Hyde Park |
| 18 Jul 1943 | Illinois Cricket Association League 1943 | | Chicago Cricket Club v South Park |
| 01 Aug 1943 | Illinois Cricket Association League 1943 | | Chicago Cricket Club v Lake Forest |
| 15 Aug 1943 | Illinois Cricket Association League 1943 | | South Park v Winnetka and Oak Park |
| 03 Oct 1943 | Illinois Cricket Association League 1943 | | South Park v Winnetka and Oak Park |
| 26 Sep 1943 | Illinois Cricket Association League 1943 | Challenge Match | Chicago Cricket Club v Rest of Illinois |
| 04 Sep 1943 | Other matches in United States of America 1943 | | Illinois v Detroit West Indians |
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