| 18 Jun 1939 | Illinois Cricket Association League 1939 | | Oak Park v Washington Park |
| 02 Jul 1939 | Illinois Cricket Association League 1939 | | Oak Park v Lake Shore |
| 09 Jul 1939 | Illinois Cricket Association League 1939 | | Oak Park v Milwaukee |
| 23 Jul 1939 | Illinois Cricket Association League 1939 | | Oak Park v Lake Forest |
| 06 Aug 1939 | Illinois Cricket Association League 1939 | | Oak Park v Winnetka |
| 20 Aug 1939 | Illinois Cricket Association League 1939 | | Oak Park v River Forest |
| 24 Sep 1939 | Illinois Cricket Association League 1939 | | Oak Park v Hyde Park |
| 15 May 1938 | Illinois Cricket Association League 1938 | | Oak Park v River Forest |
| 29 May 1938 | Illinois Cricket Association League 1938 | | Oak Park v Lake Forest |
| 30 May 1938 | Illinois Cricket Association League 1938 | | Oak Park v Milwaukee |
| 05 Jun 1938 | Illinois Cricket Association League 1938 | | Oak Park v Washington Park |
| 21 Aug 1938 | Illinois Cricket Association League 1938 | | Oak Park v Hyde Park |
| 28 Aug 1938 | Illinois Cricket Association League 1938 | | Oak Park v Chicago Cricket Club |
| 28 Aug 1938 | Illinois Cricket Association League 1938 | | Oak Park v Chicago Cricket Club |
| 04 Sep 1938 | Illinois Cricket Association League 1938 | | Oak Park v Winnetka |
| 11 Sep 1938 | Century of Progress Knockout Tournament 1938 | First Round | Oak Park v Winnetka |
| 23 Jul 1938 | Other matches in United States of America 1938 | | Illinois Cricket Association Juniors v DW Catling's XI |
| 27 Aug 1938 | Other matches in United States of America 1938 | | Illinois Cricket Association Juniors v DW Catling's XI |
| 23 May 1937 | Illinois Cricket Association League 1937 | | Oak Park v Chicago Cricket Club |
| 30 May 1937 | Illinois Cricket Association League 1937 | | Garfield Park v Winnetka |
| 13 Jun 1937 | Illinois Cricket Association League 1937 | | Oak Park v Lake Shore |
| 20 Jun 1937 | Illinois Cricket Association League 1937 | | Oak Park v Garfield Park |
| 27 Jun 1937 | Illinois Cricket Association League 1937 | | Oak Park v Milwaukee |
| 11 Jul 1937 | Illinois Cricket Association League 1937 | | Oak Park v Hyde Park |
| 01 Aug 1937 | Illinois Cricket Association League 1937 | | Oak Park v Washington Park |
| 15 Aug 1937 | Illinois Cricket Association League 1937 | | Oak Park v Winnetka |
| 05 Jun 1937 | Century of Progress Knockout Tournament 1937 | First Round | Oak Park v Garfield Park |
| 05 Jul 1937 | Other matches in United States of America 1937 | | Oak Park and Garfield Park v Missouri |
| 07 Aug 1937 | Other matches in United States of America 1937 | | Oak Park v Old Timers |
| 28 Jun 1936 | Century of Progress Knockout Tournament 1936 | First Round | Oak Park v Chicago Cricket Club |
| 01 Aug 1936 | Other matches in United States of America 1936 | | Oak Park v Old Timers |
| 14 Jun 1936 | Illinois Cricket Association League 1936 | | Oak Park v Washington Park |
| 12 Jul 1936 | Illinois Cricket Association League 1936 | | Oak Park v Evanston |
| 02 Aug 1936 | Illinois Cricket Association League 1936 | | Oak Park v Lake Forest |
| 09 Aug 1936 | Illinois Cricket Association League 1936 | | Oak Park v Chicago Cricket Club |
| 16 Aug 1936 | Illinois Cricket Association League 1936 | | Oak Park v Milwaukee |
| 30 Aug 1936 | Illinois Cricket Association League 1936 | | Oak Park v Winnetka |
| 26 May 1935 | Illinois Cricket Association League 1935 | | Oak Park v Lake Forest |
| 02 Jun 1935 | Illinois Cricket Association League 1935 | | Oak Park v Chicago Cricket Club |
| 09 Jun 1935 | Illinois Cricket Association League 1935 | | Oak Park v Evanston |
| 23 Jun 1935 | Illinois Cricket Association League 1935 | | Oak Park v Milwaukee |
| 14 Jul 1935 | Illinois Cricket Association League 1935 | | Oak Park v Winnetka |
| 30 Jun 1935 | Century of Progress Knockout Tournament 1935 | First Round | Oak Park v Winnetka |
| 19 Aug 1935 | Winnipeg Junior in United States of America 1935 | | Oak Park v Winnipeg Junior |
| 21 Sep 1935 | Other matches in United States of America 1935 | | Oak Park v Old Timers |
| 27 May 1934 | Illinois Cricket Association League 1934 | | Oak Park v Chicago Cricket Club |
| 03 Jun 1934 | Illinois Cricket Association League 1934 | | Oak Park v Washington Park |
| 24 Jun 1934 | Illinois Cricket Association League 1934 | | Oak Park v Lake Forest |
| 29 Jul 1934 | Illinois Cricket Association League 1934 | | Oak Park v Chicago Cricket Club |
| 19 Aug 1934 | Illinois Cricket Association League 1934 | | Oak Park v Evanston |
| 03 Sep 1934 | Illinois Cricket Association League 1934 | | Oak Park v Winnetka |
| 23 Sep 1934 | Illinois Cricket Association League 1934 | | Oak Park v Milwaukee |
| 30 Nov 1939 | Illinois Cricket Association League 1940 | | Oak Park v River Forest |
| 12 May 1940 | Illinois Cricket Association League 1940 | | Oak Park v Washington Park |
| 02 Jun 1940 | Illinois Cricket Association League 1940 | | Oak Park v Hyde Park |
| 16 Jun 1940 | Illinois Cricket Association League 1940 | | Oak Park v Lake Forest |
| 23 Jun 1940 | Illinois Cricket Association League 1940 | | Oak Park v Lake Shore |
| 14 Jul 1940 | Illinois Cricket Association League 1940 | | Oak Park v Milwaukee |
| 28 Jul 1940 | Illinois Cricket Association League 1940 | | Oak Park v Winnetka |
| 11 Aug 1940 | Illinois Cricket Association League 1940 | | Oak Park v Chicago Cricket Club |
| 15 Sep 1940 | Century of Progress Knockout Tournament 1940 | Semi-Final | Oak Park v Winnetka |
| 10 Aug 1940 | Other matches in United States of America 1940 | | Oak Park v Old Timers |
| 18 May 1941 | Illinois Cricket Association League 1941 | | Oak Park v Lake Forest |
| 30 May 1941 | Illinois Cricket Association League 1941 | | Oak Park v Winnetka |
| 08 Jun 1941 | Illinois Cricket Association League 1941 | | Oak Park v Hyde Park |
| 29 Jun 1941 | Illinois Cricket Association League 1941 | | Oak Park v Washington Park |
| 20 Jul 1941 | Illinois Cricket Association League 1941 | | Oak Park v Chicago Cricket Club |
| 17 Aug 1941 | Illinois Cricket Association League 1941 | | Oak Park v South Park |
| 21 Sep 1941 | Illinois Cricket Association League 1941 | | Oak Park v Lake Shore |
| 19 Jul 1941 | Other matches in United States of America 1941 | | Oak Park v Old Timers |
| 21 Jun 1942 | Illinois Cricket Association League 1942 | | Oak Park v South Park |
| 26 Jul 1942 | Illinois Cricket Association League 1942 | | Oak Park v Winnetka |
| 16 Aug 1942 | Illinois Cricket Association League 1942 | | Oak Park v Chicago Cricket Club |
| 06 Sep 1942 | Illinois Cricket Association League 1942 | | Oak Park v Hyde Park |
| 11 Oct 1942 | Illinois Cricket Association League 1942 | | Oak Park v Lake Forest |
| 30 Nov 1941 | Illinois Cricket Association League 1942 | | Oak Park v Milwaukee |
| 12 Jul 1942 | Century of Progress Knockout Tournament 1942 | First Round | Oak Park v South Park |
| 18 Jul 1942 | Other matches in United States of America 1942 | | Oak Park v Old Timers |
| 13 Jun 1943 | Illinois Cricket Association League 1943 | | Oak Park v Hyde Park |
| 08 Aug 1943 | Illinois Cricket Association League 1943 | | Winnetka and Oak Park v Chicago Cricket Club |
| 17 Jul 1943 | Other matches in United States of America 1943 | | Oak Park v Old Timers |
| 24 Aug 1933 | Winnipeg St George's in United States of America 1933 | | Pakenham's Oak Park XI v Winnipeg St George's |
| 22 May 1897 | Chicago Cricket Association Walker Cup 1897 | | Oak Park v St George's Club of Chicago |
| 30 Jun 1897 | Chicago Cricket Association Walker Cup 1897 | | Oak Park v Wanderers |
| 31 Jul 1897 | Chicago Cricket Association Walker Cup 1897 | | Oak Park v Chicago Cricket Club |
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