| 11 Sep 1920 | Toronto and District Cricket Council League 1920 | Semi-Final | Grace Church v Rosedale |
| 15 May 1920 | Other matches in Canada 1920 | | Upper Canada College Second XI v Oakwood |
| 22 Jun 1895 | Other matches in Canada 1895 | | Upper Canada College v Trinity College School |
| 19 Jun 1897 | Other matches in Canada 1897 | | Upper Canada College v Trinity College School |
| 04 Sep 1897 | Other matches in Canada 1897 | | North Toronto v Woodbine |
| 20 Jun 1891 | Other matches in Canada 1891 | | Deer Park v Surrey |
| 18 Jul 1891 | Other matches in Canada 1891 | | Deer Park v Toronto Junction |
| 21 Jun 1890 | Other matches in Canada 1890 | | Deer Park v Rosedale |
| 23 Aug 1890 | Other matches in Canada 1890 | | Deer Park v East Toronto |
| 12 Jul 1890 | Other matches in Canada 1890 | | Deer Park v St James' Cathedral |
| 01 Jul 1889 | Other matches in Canada 1889 | | Deer Park v Parkdale |
| 13 Jul 1889 | Other matches in Canada 1889 | | Deer Park v St James' Cathedral |
| 27 Jul 1889 | Other matches in Canada 1889 | | Deer Park v Gooderham and Worts Distillery |
| 14 Jun 1890 | Other matches in Canada 1890 | | Deer Park v St James' Cathedral Second XI |
| 20 Jun 1903 | Other matches in Canada 1903 | | Upper Canada College v Trinity College School |
| 30 May 1905 | Other matches in Canada 1905 | | Upper Canada College v Trinity College School |
| 06 Jun 1908 | Other matches in Canada 1908 | | Upper Canada College v Ridley College |
| 15 Jun 1918 | Other matches in Canada 1918 | | Upper Canada College v Ridley College |
| 16 Jun 1906 | Other matches in Canada 1906 | | Upper Canada College v Ridley College |
| 12 Jun 1909 | Other matches in Canada 1909 | | Upper Canada College v St Andrew's College |
| 29 May 1918 | Other matches in Canada 1918 | | Upper Canada College v St Andrew's College |
| 06 Jun 1903 | Other matches in Canada 1903 | | Upper Canada College v St Andrew's College |
| 08 Jun 1907 | Other matches in Canada 1907 | | Upper Canada College v St Andrew's College |
| 06 Jun 1917 | Other matches in Canada 1917 | | Upper Canada College v St Andrew's College |
| 22 Jun 1909 | Haverford College in Canada 1909 | | Upper Canada College v Haverford College |
| 04 Jul 1857 | Other matches in Canada 1857 | | Carlton Club of Toronto v Upper Canada College |
| 18 Jul 1857 | Other matches in Canada 1857 | | Upper Canada College v Toronto Second XI |
| 22 Jul 1857 | Other matches in Canada 1857 | | Upper Canada College v Toronto Second XI |
| 24 Jun 1875 | Other matches in Canada 1875 | | Toronto Juniors v Upper Canada College |
| 20 May 1876 | Other matches in Canada 1876 | | Upper Canada College v Toronto University |
| 19 Jun 1886 | Other matches in Canada 1886 | | Upper Canada College Second XI v Hamilton Second XI |
| 06 May 1911 | Other matches in Canada 1911 | | Upper Canada College v Rosedale |
| 03 Jun 1911 | Other matches in Canada 1911 | | Upper Canada College v St Andrew's College |
| 08 May 1915 | Other matches in Canada 1915 | | Upper Canada College v Grace Church |
| 05 Jun 1915 | Other matches in Canada 1915 | | Upper Canada College v Upper Canada College Old Boys |
| 04 May 1918 | Other matches in Canada 1918 | | Upper Canada College v Old Country Club |
| 08 Jun 1918 | Other matches in Canada 1918 | | Upper Canada College v Upper Canada College Old Boys |
| 15 Jun 1918 | Other matches in Canada 1918 | | Upper Canada College Second XI v Ridley College Second XI |
| 06 Sep 1919 | Other matches in Canada 1919 | | Dovercourt v St George's Club of Hamilton |
| 02 Aug 1919 | Church and Mercantile Cricket League 1919 | | St Edmund's v Dovercourt |
| 09 Aug 1919 | Church and Mercantile Cricket League 1919 | | St Edmund's v St Matthias |
| 16 Aug 1919 | Church and Mercantile Cricket League 1919 | | St Edmund's v Yorkshire Society |
| 30 Aug 1919 | Church and Mercantile Cricket League 1919 | | Dovercourt v St Edmund's |
| 13 Sep 1919 | Church and Mercantile Cricket League 1919 | | St Edmund's v Woodgreen Brotherhood |
| 24 Jul 1875 | Other matches in Canada 1875 | | Upper Canada College v Trinity College School |
| 08 May 1901 | Other matches in Canada 1901 | | Upper Canada College v University of Trinity College |
| 11 May 1901 | Other matches in Canada 1901 | | Upper Canada College v Gordon, Mackay and Company |
| 18 May 1901 | Other matches in Canada 1901 | | Upper Canada College v Toronto Cricket Club |
| 07 Jun 1901 | Other matches in Canada 1901 | | Upper Canada College v Toronto University |
| 15 Jun 1901 | Other matches in Canada 1901 | | Upper Canada College Past and Present Day Boys v Upper Canada College Past and Present Boarders |
| 19 Jun 1901 | Other matches in Canada 1901 | | Upper Canada College v Gordon, Mackay and Company |
| 16 Jun 1898 | Other matches in Canada 1898 | | Upper Canada College v Ottawa |
| 13 Jun 1934 | Other matches in Canada 1934 | | Upper Canada College v Ridley College |
| 05 Jun 1935 | Other matches in Canada 1935 | | Upper Canada College v Trinity College School |
| 10 Jun 1935 | Other matches in Canada 1935 | | Upper Canada College v St Andrew's College |
| 12 Jun 1935 | Other matches in Canada 1935 | | Upper Canada College v Ridley College |
| 05 Jun 1936 | Other matches in Canada 1936 | | Upper Canada College v Ridley College |
| 05 Jun 1937 | Other matches in Canada 1937 | | Upper Canada College v Trinity College School |
| 08 Jun 1938 | Other matches in Canada 1938 | | Upper Canada College v Ridley College |
| 03 Jun 1939 | Other matches in Canada 1939 | | Upper Canada College v Trinity College School |
| 07 Jun 1939 | Other matches in Canada 1939 | | Upper Canada College v St Andrew's College |
| 06 Jul 1913 | Other matches in Canada 1913 | | Upper Canada College v St Andrew's College |
| 27 May 1948 | Other matches in Canada 1948 | | Upper Canada College Juniors v Trinity College School Juniors |
| 27 May 1948 | Other matches in Canada 1948 | | Upper Canada College Juniors Second XI v Trinity College School Juniors Second XI |
| 30 Jun 1888 | Other matches in Canada 1888 | | Deer Park v East Toronto |
| 02 Jul 1888 | Other matches in Canada 1888 | | Deer Park v Parkdale Juniors |
| 07 Jul 1888 | Other matches in Canada 1888 | | Deer Park v Agricultural Insurance Company |
| 14 Jul 1888 | Other matches in Canada 1888 | | Deer Park v Parkdale |
| 21 Jul 1888 | Other matches in Canada 1888 | | Deer Park v St James' Cathedral |
| 28 Jul 1888 | Other matches in Canada 1888 | | Deer Park v St Matthias |
| 13 Aug 1888 | Other matches in Canada 1888 | | Deer Park v East Toronto |
| 18 Aug 1888 | Other matches in Canada 1888 | | Deer Park v St Matthias |
| 22 Sep 1888 | Other matches in Canada 1888 | | Deer Park v Agricultural Insurance Company |
| 04 Jun 1889 | Other matches in Canada 1889 | | Deer Park v Toronto University |
| 29 Jun 1889 | Other matches in Canada 1889 | | Deer Park v East Toronto |
| 06 Jul 1889 | Other matches in Canada 1889 | | Deer Park v Parkdale Colts |
| 17 Aug 1889 | Other matches in Canada 1889 | | Deer Park v Pacific Club of Toronto Junction |
| 30 May 1891 | Other matches in Canada 1891 | | Deer Park v Toronto Colts |
| 25 Jul 1891 | Other matches in Canada 1891 | | Deer Park v East Toronto |
| 28 May 1898 | Other matches in Canada 1898 | | Upper Canada College v Toronto-Rosedale |
| 12 Jun 1900 | Other matches in Canada 1900 | | Upper Canada College v McGill University |
| 06 May 1911 | Other matches in Canada 1911 | | Upper Canada College Second XI v Rosedale Second XI |
| 13 May 1911 | Other matches in Canada 1911 | | Upper Canada College v Grace Church |
| 20 May 1911 | Other matches in Canada 1911 | | Upper Canada College v Aura Lee |
| 08 Jun 1911 | Other matches in Canada 1911 | | Upper Canada College v Toronto |
| 11 May 1918 | Other matches in Canada 1918 | | Upper Canada College v Albion Club of Toronto |
| 02 Aug 1919 | Other matches in Canada 1919 | | Grand Trunk Railway v Oakwood Boys |
| 30 Aug 1919 | Other matches in Canada 1919 | | St Chad's v Oakwood |
| 13 Sep 1919 | Other matches in Canada 1919 | | Grand Trunk Railway v Oakwood |
| 01 Jun 1959 | Other matches in Canada 1959 | | Upper Canada College v Ridley College |
| 03 May 1919 | Other matches in Canada 1919 | | Upper Canada College v St Cyprian's |
| 17 May 1919 | Other matches in Canada 1919 | | Upper Canada College v Old Country Club |
| 31 May 1919 | Other matches in Canada 1919 | | Upper Canada College v West Toronto |
| 07 Jun 1919 | Other matches in Canada 1919 | | Upper Canada College Second XI v Oakwood |
| 31 May 1899 | Other matches in Canada 1899 | | Upper Canada College v Toronto University |
| 03 Jun 1899 | Other matches in Canada 1899 | | Upper Canada College v Anchorage Club of Oakville |
| 10 Jun 1899 | Other matches in Canada 1899 | | Upper Canada College v Upper Canada College Old Boys |
| 14 Jun 1899 | Other matches in Canada 1899 | | Upper Canada College v Hamilton |
| 18 Aug 1899 | Other matches in Canada 1899 | | St Cyprian's v Orillia |
| 19 Aug 1899 | Other matches in Canada 1899 | | Upper Canada College v Orillia |
| 19 May 1900 | Other matches in Canada 1900 | | Upper Canada College v St Alban's Cathedral |
| 22 Jun 1901 | Other matches in Canada 1901 | | Upper Canada College Second XI v St Alban's Cathedral Second XI |
| 02 May 1903 | Other matches in Canada 1903 | | Upper Canada College v University of Trinity College |
| 09 May 1903 | Other matches in Canada 1903 | | Upper Canada College v Grace Church |
| 16 May 1903 | Other matches in Canada 1903 | | Upper Canada College Crusaders v Upper Canada College Devonshires |
| 20 May 1903 | Other matches in Canada 1903 | | Upper Canada College v Upper Canada College Masters |
| 30 May 1903 | Other matches in Canada 1903 | | Upper Canada College Second XI v St Alban's Cathedral |
| 10 Jun 1903 | Other matches in Canada 1903 | | Upper Canada College v Toronto |
| 07 May 1904 | Other matches in Canada 1904 | | Upper Canada College v St Simon's Church |
| 07 May 1904 | Other matches in Canada 1904 | | Upper Canada College Second XI v St Stephen's Church |
| 09 May 1904 | Other matches in Canada 1904 | | Upper Canada College v Steeplechase |
| 11 May 1904 | Other matches in Canada 1904 | | Upper Canada College v University of Trinity College |
| 14 May 1904 | Other matches in Canada 1904 | | Upper Canada College Third XI v Highfield School |
| 16 May 1904 | Other matches in Canada 1904 | | Upper Canada College Cavaliers v Upper Canada College Junior Day Boys |
| 19 May 1904 | Other matches in Canada 1904 | | Upper Canada College Crusaders v Upper Canada College Junior Day Boys |
| 21 May 1904 | Other matches in Canada 1904 | | Upper Canada College v St Alban's Cathedral |
| 21 May 1904 | Other matches in Canada 1904 | | Upper Canada College Second XI v St Alban's Cathedral Second XI |
| 23 May 1904 | Other matches in Canada 1904 | | Upper Canada College Cavaliers v Upper Canada College Crusaders |
| 24 May 1904 | Other matches in Canada 1904 | | Upper Canada College Third XI v Peterborough Colts |
| 25 May 1904 | Other matches in Canada 1904 | | Upper Canada College v Rosedale |
| 27 May 1904 | Other matches in Canada 1904 | | Upper Canada College Crusaders v Upper Canada College Junior Day Boys |
| 28 May 1904 | Other matches in Canada 1904 | | Upper Canada College v Toronto |
| 30 May 1904 | Other matches in Canada 1904 | | Upper Canada College Preparatory School v St Andrew's College Preparatory School |
| 30 May 1904 | Other matches in Canada 1904 | | Upper Canada College Second XI v St Alban's Cathedral Second XI |
| 31 May 1904 | Other matches in Canada 1904 | | Upper Canada College Cavaliers v Upper Canada College Junior Day Boys |
| 03 Jun 1904 | Other matches in Canada 1904 | | Upper Canada College Crusaders v Upper Canada College Junior Day Boys |
| 04 Jun 1904 | Other matches in Canada 1904 | | Upper Canada College Second XI v Toronto Electric Light Company |
| 06 Jun 1904 | Other matches in Canada 1904 | | Upper Canada College Cavaliers v Upper Canada College Crusaders |
| 07 Jun 1904 | Other matches in Canada 1904 | | Upper Canada College v Toronto University |
| 10 Jun 1904 | Other matches in Canada 1904 | | Upper Canada College Cavaliers v Upper Canada College Crusaders |
| 11 Jun 1904 | Other matches in Canada 1904 | | Upper Canada College v Upper Canada College Old Boys |
| 11 Jun 1904 | Other matches in Canada 1904 | | Upper Canada College Second XI v Upper Canada College Old Boys Second XI |
| 13 Jun 1904 | Other matches in Canada 1904 | | Upper Canada College Cavaliers v Upper Canada College Junior Day Boys |
| 18 Jun 1904 | Other matches in Canada 1904 | | Upper Canada College Second XI v St Stephen's Church |
| 24 Jun 1904 | Other matches in Canada 1904 | | Upper Canada College v Royal Military College |
| 20 Aug 1904 | Junior Cricket League 1904 | | Deer Park v Grace Church Second XI |
| 30 Nov 1904 | Church and Mercantile Cricket League 1905 | Eastern Section | Deer Park v St Clement's |
| 30 Nov 1904 | Church and Mercantile Cricket League 1905 | Eastern Section | Deer Park v St George's Club of Toronto |
| 20 May 1905 | Other matches in Canada 1905 | | Upper Canada College v St Simon's Church |
| 27 May 1905 | Other matches in Canada 1905 | | Upper Canada College v St Alban's Cathedral |
| 27 May 1905 | Other matches in Canada 1905 | | Upper Canada College Second XI v St Alban's Cathedral Second XI |
| 17 Jun 1905 | Other matches in Canada 1905 | | Upper Canada College v St Andrew's College |
| 24 Jun 1905 | Other matches in Canada 1905 | | Upper Canada College v Trinity College School |
| 26 Jun 1905 | Other matches in Canada 1905 | | Upper Canada College v Royal Military College |
| 15 Jul 1905 | Church and Mercantile Cricket League 1905 | Eastern Section | Deer Park v Rosedale Juniors |
| 22 Jul 1905 | Other matches in Canada 1905 | | Deer Park v Yorkshire Society |
| 05 Aug 1905 | Church and Mercantile Cricket League 1905 | Eastern Section | Deer Park v Ontario Accident Insurance Company |
| 12 Aug 1905 | Church and Mercantile Cricket League 1905 | Eastern Section | Deer Park v Grace Church |
| 26 Aug 1905 | Other matches in Canada 1905 | | Deer Park v Dovercourt |
| 07 May 1906 | Other matches in Canada 1906 | | Upper Canada College v RY Cory's XI |
| 09 May 1906 | Other matches in Canada 1906 | | Upper Canada College v Gordon, Mackay and Company |
| 12 May 1906 | Other matches in Canada 1906 | | Upper Canada College v St Alban's Cathedral |
| 19 May 1906 | Other matches in Canada 1906 | | Upper Canada College v RY Cory's XI |
| 19 May 1906 | Other matches in Canada 1906 | | Upper Canada College Second XI v St Andrew's College Second XI |
| 29 May 1906 | Other matches in Canada 1906 | | Upper Canada College v University of Trinity College |
| 29 May 1906 | Other matches in Canada 1906 | | Upper Canada College Second XI v Upper Canada College Cavaliers and Crusaders |
| 30 May 1906 | Other matches in Canada 1906 | | Upper Canada College Second XI v St Alban's Cathedral School |
| 09 Jun 1906 | Church and Mercantile Cricket League 1906 | Eastern Section | Deer Park v St Barnabas |
| 25 Jun 1906 | Other matches in Canada 1906 | | Upper Canada College v Royal Military College |
| 30 Jun 1906 | Church and Mercantile Cricket League 1906 | Eastern Section | Deer Park v Rosedale |
| 07 Jul 1906 | Other matches in Canada 1906 | | Deer Park v Yorkshire Society |
| 14 Jul 1906 | Church and Mercantile Cricket League 1906 | Eastern Section | Deer Park v Ontario Accident Insurance Company |
| 28 Jul 1906 | Other matches in Canada 1906 | | Deer Park v St Clement's |
| 04 Aug 1906 | Church and Mercantile Cricket League 1906 | Eastern Section | Deer Park v St Clement's |
| 18 Aug 1906 | Other matches in Canada 1906 | | Deer Park v St Cyprian's |
| 11 May 1907 | Other matches in Canada 1907 | | Upper Canada College v St Alban's Cathedral |
| 11 May 1907 | Other matches in Canada 1907 | | Upper Canada College Second XI v St Alban's Cathedral |
| 14 Jun 1907 | Other matches in Canada 1907 | | Upper Canada College v Upper Canada College Old Boys |
| 06 Jul 1907 | Other matches in Canada 1907 | | Deer Park v St Cyprian's |
| 13 Jul 1907 | Church and Mercantile Cricket League 1907 | Eastern Section | Deer Park v Aura Lee |
| 03 Aug 1907 | Church and Mercantile Cricket League 1907 | Eastern Section | Deer Park v St Matthew's |
| 17 Aug 1907 | Church and Mercantile Cricket League 1907 | Eastern Section | Deer Park v St Clement's |
| 24 Aug 1907 | Church and Mercantile Cricket League 1907 | Eastern Section | Deer Park v Yorkshire Society |
| 09 May 1908 | Other matches in Canada 1908 | | Upper Canada College v Grace Church |
| 09 May 1908 | Other matches in Canada 1908 | | Upper Canada College Second XI v Grace Church Second XI |
| 17 Jun 1908 | Other matches in Canada 1908 | | Upper Canada College v Grace Church |
| 22 Jun 1908 | Other matches in Canada 1908 | | Upper Canada College v Rosedale |
| 04 Jul 1908 | Other matches in Canada 1908 | | Deer Park v Rosedale |
| 11 Jul 1908 | Other matches in Canada 1908 | | Deer Park v Yorkshire Society |
| 01 Aug 1908 | Other matches in Canada 1908 | | Deer Park v Toronto |
| 08 Aug 1908 | Other matches in Canada 1908 | | Deer Park v St Alban's Cathedral |
| 15 Aug 1908 | Other matches in Canada 1908 | | Deer Park v Grace Church |
| 22 Aug 1908 | Other matches in Canada 1908 | | Deer Park v Toronto |
| 29 Aug 1908 | Other matches in Canada 1908 | | Deer Park v Parkdale |
| 30 Nov 1908 | Toronto City Cricket League 1909 | | Deer Park v Grace Church |
| 15 May 1909 | Other matches in Canada 1909 | | Upper Canada College v St Alban's Cathedral |
| 15 May 1909 | Other matches in Canada 1909 | | Upper Canada College Second XI v St Alban's Cathedral Second XI |
| 19 May 1909 | Other matches in Canada 1909 | | Upper Canada College v Toronto |
| 22 May 1909 | Other matches in Canada 1909 | | Upper Canada College v St Paul's Church |
| 29 May 1909 | Other matches in Canada 1909 | | Deer Park v Upper Canada College |
| 29 May 1909 | Other matches in Canada 1909 | | Upper Canada College v Toronto University |
| 16 Jun 1909 | Other matches in Canada 1909 | | Upper Canada College v Royal Military College Cadets |
| 10 Jul 1909 | Toronto City Cricket League 1909 | | Deer Park v St Alban's Cathedral |
| 31 Jul 1909 | Other matches in Canada 1909 | | Deer Park v Parkdale |
| 21 Aug 1909 | Toronto City Cricket League 1909 | | Deer Park v Toronto Amateur Athletic Association |
| 28 Aug 1909 | Toronto City Cricket League 1909 | | Deer Park v Toronto |
| 14 May 1910 | Other matches in Canada 1910 | | Upper Canada College v St Paul's Church |
| 21 May 1910 | Other matches in Canada 1910 | | Upper Canada College v Toronto |
| 28 May 1910 | Other matches in Canada 1910 | | Upper Canada College v St Alban's Cathedral |
| 28 May 1910 | Other matches in Canada 1910 | | Upper Canada College Second XI v St Alban's Cathedral Second XI |
| 04 Jun 1910 | Other matches in Canada 1910 | | Upper Canada College v Deer Park |
| 04 Jun 1910 | Other matches in Canada 1910 | | Upper Canada College Second XI v St Andrew's College Second XI |
| 09 Jul 1910 | Toronto City Cricket League 1910 | Division A | Deer Park v St Alban's Cathedral |
| 16 Jul 1910 | Toronto City Cricket League 1910 | Division A | Deer Park v Toronto |
| 30 Jul 1910 | Other matches in Canada 1910 | | Deer Park v St James' Cathedral |
| 13 Aug 1910 | Toronto City Cricket League 1910 | Division A | Deer Park v Grace Church |
| 20 Aug 1910 | Toronto City Cricket League 1910 | Division A | Deer Park v Rosedale |
| 13 Jun 1930 | Haverford College in Canada 1930 | | Upper Canada College v Haverford College |
| 30 Apr 1938 | Other matches in Canada 1938 | | Upper Canada College v Scarborough |
| 30 Apr 1938 | Other matches in Canada 1938 | | Upper Canada College v Riverdale |
| 07 May 1938 | Other matches in Canada 1938 | | Upper Canada College v Yorkshire Society |
| 07 May 1938 | Other matches in Canada 1938 | | Upper Canada College v Dentonia Park |
| 07 May 1938 | Other matches in Canada 1938 | | Upper Canada College Under-16s v Dentonia Park Second XI |
| 14 May 1938 | Other matches in Canada 1938 | | Upper Canada College Second XI v Toronto Second XI |
| 21 May 1938 | Other matches in Canada 1938 | | Upper Canada College v St Edmund's |
| 21 May 1938 | Other matches in Canada 1938 | | Upper Canada College v Scarborough |
| 24 May 1938 | Other matches in Canada 1938 | | Upper Canada College v Upper Canada College Old Boys |
| 28 May 1938 | Other matches in Canada 1938 | | Upper Canada College v Riverdale |
| 23 Jun 1888 | Other matches in Canada 1888 | | Deer Park v East Toronto Juniors |
| 17 Jun 1909 | Haverford College in Canada 1909 | | Upper Canada College v Haverford College |
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