| 04 Jun 1921 | Toronto and District Cricket Council League 1921 | | West Indian v Birchcliffe Union Congregational |
| 11 Jun 1921 | Toronto and District Cricket Council League 1921 | | St Chad's v St Edmund's |
| 18 Jun 1921 | Toronto and District Cricket Council League 1921 | | West Indian v Oakville |
| 25 Jun 1921 | Toronto and District Cricket Council League 1921 | | St Chad's v Woodgreen Brotherhood |
| 23 Jul 1921 | Toronto and District Cricket Council League 1921 | | West Indian v Kentish Association |
| 20 Aug 1921 | Toronto and District Cricket Council League 1921 | | St Chad's v St Cyprian's |
| 27 Aug 1921 | Toronto and District Cricket Council League 1921 | | West Indian v St Barnabas |
| 15 May 1920 | Other matches in Canada 1920 | | St Chad's v Dovercourt |
| 03 Jul 1920 | Other matches in Canada 1920 | | St Cyprian's v Albion Club of Toronto |
| 10 Jul 1920 | Other matches in Canada 1920 | | St Cyprian's v St George's Club of Toronto |
| 22 May 1920 | Toronto and District Cricket Council League 1920 | | St Cyprian's v St George's Club of Toronto |
| 05 Jun 1920 | Toronto and District Cricket Council League 1920 | | St Cyprian's v Yorkshire Society |
| 17 Jul 1920 | Toronto and District Cricket Council League 1920 | | St Chad's v Parkdale |
| 24 Jul 1920 | Toronto and District Cricket Council League 1920 | | St Cyprian's v Kentish Association |
| 14 Aug 1920 | Toronto and District Cricket Council League 1920 | | St Cyprian's v St Chad's |
| 21 Aug 1920 | Toronto and District Cricket Council League 1920 | | St Chad's v Broadview |
| 24 May 1920 | Other matches in Canada 1920 | | St Cyprian's v St Chad's |
| 19 Jun 1920 | Other matches in Canada 1920 | | St Cyprian's v Dovercourt |
| 13 May 1922 | Toronto and District Cricket Council League 1922 | | West Indian v Birch Cliff |
| 27 May 1922 | Toronto and District Cricket Council League 1922 | | West Indian v Kentish Association |
| 10 Jun 1922 | Toronto and District Cricket Council League 1922 | | West Indian v St Chad's |
| 17 Jun 1922 | Toronto and District Cricket Council League 1922 | | West Indian v St Barnabas |
| 19 May 1923 | Continental Life Cup 1923 | First Round | West Indian v St Chad's |
| 02 Jun 1923 | Toronto and District Cricket Council League 1923 | | West Indian v Dovercourt |
| 25 Aug 1923 | Toronto and District Cricket Council League 1923 | | West Indian v Canadian National Railway |
| 04 Jul 1914 | Church and Mercantile Cricket League 1914 | Central Section | St Cyprian's v Albion Club of Toronto |
| 23 May 1914 | Church and Mercantile Cricket League 1914 | Central Section | St Cyprian's v Bedford Park |
| 13 Jun 1914 | Church and Mercantile Cricket League 1914 | Central Section | St Cyprian's v Newmarket |
| 16 May 1914 | Church and Mercantile Cricket League 1914 | Central Section | St Cyprian's v St Clement's |
| 11 Jul 1914 | Church and Mercantile Cricket League 1914 | Central Section | St Cyprian's v St Matthias |
| 03 Jun 1911 | Church and Mercantile Cricket League 1911 | Western Section | St Cyprian's v Grace Church |
| 17 Jun 1911 | Church and Mercantile Cricket League 1911 | Western Section | St Cyprian's v Robert Simpson Company |
| 10 Jun 1911 | Church and Mercantile Cricket League 1911 | Western Section | St Cyprian's v West Toronto |
| 22 Jun 1912 | Church and Mercantile Cricket League 1912 | Western Section | St Cyprian's v West Toronto |
| 29 Jun 1912 | Church and Mercantile Cricket League 1912 | Western Section | St Cyprian's v Old Country Club |
| 06 Jul 1912 | Church and Mercantile Cricket League 1912 | Western Section | St Cyprian's v Old Country Club |
| 20 Jul 1912 | Church and Mercantile Cricket League 1912 | Western Section | St Cyprian's v Garrett |
| 27 Jul 1912 | Church and Mercantile Cricket League 1912 | Western Section | St Cyprian's v Dovercourt |
| 03 Aug 1912 | Church and Mercantile Cricket League 1912 | Western Section | St Cyprian's v St Edmund's |
| 08 Jun 1912 | Other matches in Canada 1912 | | Yorkshire Society v St Edmund's |
| 26 Jul 1913 | Church and Mercantile Cricket League 1913 | Western Section | St Cyprian's v Garrett |
| 30 Aug 1913 | Church and Mercantile Cricket League 1913 | Western Section | St Cyprian's v Old Country Club |
| 28 Jun 1913 | Church and Mercantile Cricket League 1913 | Western Section | St Cyprian's v Yorkshire Society |
| 12 Jul 1913 | Church and Mercantile Cricket League 1913 | Western Section | St Cyprian's v Dovercourt |
| 19 Jul 1913 | Church and Mercantile Cricket League 1913 | Western Section | St Cyprian's v West Toronto |
| 16 Aug 1913 | Church and Mercantile Cricket League 1913 | Western Section | St Cyprian's v St Edmund's |
| 23 Aug 1913 | Church and Mercantile Cricket League 1913 | Western Section | St Cyprian's v Old Country Club |
| 02 Aug 1913 | Other matches in Canada 1913 | | St Cyprian's v Mimico Old Country Club |
| 06 Sep 1913 | Other matches in Canada 1913 | | St Cyprian's v St Matthias |
| 05 Jun 1915 | Church and Mercantile Cricket League 1915 | Central Section | St George's Club of Toronto v St Cyprian's |
| 12 Jun 1915 | Church and Mercantile Cricket League 1915 | Central Section | St George's Club of Toronto v St Matthias |
| 17 Jul 1915 | Church and Mercantile Cricket League 1915 | Central Section | St George's Club of Toronto v Albion Club of Toronto |
| 14 Aug 1915 | Church and Mercantile Cricket League 1915 | Central Section | St Cyprian's v Albion Club of Toronto |
| 15 May 1915 | Other matches in Canada 1915 | | St Cyprian's v St George's Club of Toronto |
| 22 May 1915 | Other matches in Canada 1915 | | St Cyprian's v Mimico Old Country Club |
| 26 Jun 1915 | Other matches in Canada 1915 | | St Cyprian's v Parkdale |
| 10 Jul 1915 | Other matches in Canada 1915 | | St George's Club of Toronto v St Mark's |
| 24 Jul 1915 | Church and Mercantile Cricket League 1915 | Central Section | St Cyprian's v St George's Club of Toronto |
| 07 Aug 1915 | Other matches in Canada 1915 | | St George's Club of Toronto v Evangelia |
| 21 Aug 1915 | Church and Mercantile Cricket League 1915 | Central Section | St George's Club of Toronto v Newmarket |
| 04 Sep 1915 | Church and Mercantile Cricket League 1915 | Central Section | St Cyprian's v Eaton's |
| 30 May 1914 | Other matches in Canada 1914 | | St Cyprian's B v St Edmund's B |
| 01 Aug 1914 | Other matches in Canada 1914 | | St Cyprian's v St George's Club of Toronto |
| 08 Aug 1914 | Other matches in Canada 1914 | | St George's Club of Toronto v Olivet |
| 15 Aug 1914 | Other matches in Canada 1914 | | St George's Club of Toronto v St Edmund's |
| 28 Aug 1915 | Church and Mercantile Cricket League 1915 | Central Section | St George's Club of Toronto v Eaton's |
| 18 May 1918 | Church and Mercantile Cricket League 1918 | | St Cyprian's v Yorkshire Society |
| 25 May 1918 | Church and Mercantile Cricket League 1918 | | St Cyprian's v West Toronto |
| 01 Jun 1918 | Church and Mercantile Cricket League 1918 | | St Cyprian's v Dovercourt |
| 22 Jun 1918 | Church and Mercantile Cricket League 1918 | | St Cyprian's v Old Country Club |
| 06 Jul 1918 | Church and Mercantile Cricket League 1918 | | St Cyprian's v St Edmund's |
| 13 Jul 1918 | Church and Mercantile Cricket League 1918 | | St Cyprian's v Broadview |
| 31 Aug 1918 | Church and Mercantile Cricket League 1918 | | St Cyprian's v Albion Club of Toronto |
| 13 Sep 1919 | Other matches in Canada 1919 | | St Cyprian's v St Matthias |
| 05 Jul 1919 | Church and Mercantile Cricket League 1919 | | St Cyprian's v West Indian |
| 26 Jul 1919 | Church and Mercantile Cricket League 1919 | | St Cyprian's v Dovercourt |
| 02 Aug 1919 | Church and Mercantile Cricket League 1919 | | West Indian v Yorkshire Society |
| 09 Aug 1919 | Church and Mercantile Cricket League 1919 | | St Cyprian's v Broadview |
| 16 Aug 1919 | Church and Mercantile Cricket League 1919 | | St Matthias v St Cyprian's |
| 30 Aug 1919 | Church and Mercantile Cricket League 1919 | | West Indian v Broadview |
| 06 Sep 1919 | Church and Mercantile Cricket League 1919 | | West Indian v St Cyprian's |
| 14 Jun 1919 | Church and Mercantile Cricket League 1919 | | West Indian v Dovercourt |
| 28 Jun 1919 | Church and Mercantile Cricket League 1919 | | St Cyprian's v St Edmund's |
| 07 Jun 1919 | Church and Mercantile Cricket League 1919 | | St Cyprian's v Yorkshire Society |
| 24 May 1919 | Church and Mercantile Cricket League 1919 | | West Indian v St Edmund's |
| 31 May 1919 | Church and Mercantile Cricket League 1919 | | West Indian v St Matthias |
| 19 Jul 1919 | Church and Mercantile Cricket League 1919 | | West Indian v Woodgreen Brotherhood |
| 20 May 1911 | Other matches in Canada 1911 | | St Cyprian's v Eaton's |
| 15 Jun 1912 | Other matches in Canada 1912 | | Evangelia v Eaton's |
| 17 Aug 1912 | Other matches in Canada 1912 | | St Cyprian's v East Toronto |
| 21 Sep 1912 | Other matches in Canada 1912 | | St Cyprian's v St Alban's Cathedral |
| 13 Sep 1913 | Other matches in Canada 1913 | | St Cyprian's v St Alban's Cathedral |
| 20 Jun 1914 | Other matches in Canada 1914 | | St George's Club of Toronto v St Edmund's B |
| 27 Jun 1914 | Other matches in Canada 1914 | | St Cyprian's v St George's Club of Oshawa |
| 18 Jul 1914 | Other matches in Canada 1914 | | St George's Club of Toronto v West Toronto B |
| 25 Jul 1914 | Other matches in Canada 1914 | | St Cyprian's v Woodgreen Brotherhood |
| 25 Jul 1914 | Other matches in Canada 1914 | | St George's Club of Toronto v Riverdale B |
| 22 Aug 1914 | Other matches in Canada 1914 | | St George's Club of Toronto v Dovercourt |
| 29 Aug 1914 | Other matches in Canada 1914 | | St George's Club of Toronto v Old Country Club |
| 05 Sep 1914 | Other matches in Canada 1914 | | St George's Club of Toronto v St Matthias |
| 19 Jun 1915 | Church and Mercantile Cricket League 1915 | Central Section | St Cyprian's v Newmarket |
| 18 Sep 1915 | Other matches in Canada 1915 | | St Cyprian's v Toronto Electric Light Company |
| 21 Jul 1917 | Church and Mercantile Cricket League 1917 | Eastern Section | St Cyprian's v Woodgreen Brotherhood |
| 26 May 1917 | Other matches in Canada 1917 | | St Cyprian's v St Edmund's |
| 28 Jul 1917 | Church and Mercantile Cricket League 1917 | Eastern Section | St Cyprian's v Broadview |
| 14 Jul 1917 | Church and Mercantile Cricket League 1917 | Eastern Section | St Cyprian's v Albion Club of Toronto |
| 01 Sep 1917 | Other matches in Canada 1917 | | St Cyprian's v St Edmund's |
| 24 May 1918 | Other matches in Canada 1918 | | St Cyprian's v St Edmund's |
| 21 Jun 1919 | Church and Mercantile Cricket League 1919 | | St Cyprian's v Woodgreen Brotherhood |
| 29 May 1920 | Toronto and District Cricket Council League 1920 | | St Chad's v Oakville |
| 12 Jun 1920 | Other matches in Canada 1920 | | St Chad's v Grand Trunk Railway |
| 20 Sep 1913 | Other matches in Canada 1913 | | St Cyprian's v Yorkshire Society |
| 25 May 1914 | Other matches in Canada 1914 | | Olivet v St George's Club of Toronto |
| 06 Aug 1917 | Other matches in Canada 1917 | | St Cyprian's v Old Country Club |
| 11 Aug 1917 | Other matches in Canada 1917 | | St Cyprian's v St Edmund's |
| 25 Aug 1917 | Other matches in Canada 1917 | | St Cyprian's v Dovercourt |
| 11 Sep 1909 | Other matches in Canada 1909 | | St Cyprian's v Riverdale |
| 18 Sep 1909 | Other matches in Canada 1909 | | St Cyprian's v St Mary Magdalene |
| 25 Sep 1909 | Other matches in Canada 1909 | | St Cyprian's v St David's |
| 30 Nov 1909 | Church and Mercantile Cricket League 1910 | Western Section | St Cyprian's v St Mary Magdalene |
| 30 Nov 1909 | Church and Mercantile Cricket League 1910 | Western Section | St Mary Magdalene v Garrett |
| 30 Nov 1909 | Church and Mercantile Cricket League 1910 | Western Section | St Mary Magdalene v Pioneer Adult School |
| 30 Nov 1909 | Church and Mercantile Cricket League 1910 | Western Section | St Mary Magdalene v St Cyprian's |
| 14 May 1910 | Other matches in Canada 1910 | | St Mary Magdalene v Birch Cliff |
| 21 May 1910 | Church and Mercantile Cricket League 1910 | Western Section | St Cyprian's v Weston |
| 28 May 1910 | Church and Mercantile Cricket League 1910 | Western Section | St Mary Magdalene v West Toronto |
| 02 Jul 1910 | Church and Mercantile Cricket League 1910 | Western Section | St Cyprian's v Pioneer Adult School |
| 23 Jul 1910 | Church and Mercantile Cricket League 1910 | Western Section | St Mary Magdalene v Dovercourt |
| 30 Jul 1910 | Church and Mercantile Cricket League 1910 | Western Section | St Cyprian's v Dovercourt |
| 06 Aug 1910 | Church and Mercantile Cricket League 1910 | Western Section | St Mary Magdalene v Weston |
| 13 Aug 1910 | Church and Mercantile Cricket League 1910 | Eastern Section | Devonian v Grace Church |
| 20 Aug 1910 | Church and Mercantile Cricket League 1910 | Eastern Section | Devonian v Bedford Park |
| 03 Sep 1910 | Church and Mercantile Cricket League 1910 | Eastern Section | Devonian v St Barnabas |
| 03 Sep 1910 | Other matches in Canada 1910 | | St Cyprian's v St Alban's Cathedral |
| 17 Sep 1910 | Church and Mercantile Cricket League 1910 | Western Section | St Cyprian's v Garrett |
| 30 Nov 1915 | Church and Mercantile Cricket League 1916 | Eastern Section | St Cyprian's v Evangelia |
| 30 Nov 1915 | Church and Mercantile Cricket League 1916 | Eastern Section | St Cyprian's v Woodgreen Brotherhood |
| 17 Jun 1916 | Church and Mercantile Cricket League 1916 | Western Section | Yorkshire Society v Old Country Club |
| 24 Jun 1916 | Church and Mercantile Cricket League 1916 | Eastern Section | St Cyprian's v St Matthias |
| 26 Aug 1916 | Other matches in Canada 1916 | | Old Country Club v Birch Cliff |
| 05 Jul 1924 | Toronto and District Cricket Council 1924 | A Division | West Indian v Bell Telephone Company |
| 12 Jul 1924 | Toronto and District Cricket Council 1924 | A Division | West Indian v St Cyprian's |
| 26 Jul 1924 | Toronto and District Cricket Council 1924 | A Division | West Indian v Riverdale |
| 23 May 1925 | Toronto and District Cricket Council 1925 | Continental Life Cup Division | West Indian v Broadview |
| 06 Jun 1925 | Toronto and District Cricket Council 1925 | Continental Life Cup Division | West Indian v St Cyprian's |
| 20 Jun 1925 | Toronto and District Cricket Council 1925 | Continental Life Cup Division | West Indian v Dovercourt |
| 08 Aug 1925 | Toronto and District Cricket Council 1925 | Continental Life Cup Division | West Indian v Woodgreen Brotherhood |
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