| | Regional 14 Boys |
| | TEAM NAME | Played | Wins | Losses | Ties | For | Against | Points | | AT HOME | | AWAY |
| | W | | L | | T | | W | L | T |
| | Results (U = UnOfficial) - All Games |
| | 1787 | Brampton East B | 0 | 1 | Clarkson | | | 1789 | North Miss. | 5 | 1 | Barrie | | |
| | 1790 | Milton | 0 | 3 | Oakville B | | | 1791 | Dixie A | 5 | 1 | Dixie B | | |
| | 1792 | Barrie | 6 | 0 | Milton | | | 1793 | Brampton B | 2 | 4 | North Miss. | | |
| | 1794 | Oakville B | 3 | 2 | Dixie A | | | 1795 | Dixie B | 1 | 1 | Brampton East B | | |
| | 1797 | Brampton East B | 1 | 2 | Oakville B | | | 1798 | Milton | 2 | 5 | Brampton B | | |
| | 1799 | Dixie A | 0 | 2 | Barrie | | | 1800 | Clarkson | 6 | 0 | Dixie B | | |
| | 1803 | Barrie | 2 | 0 | Brampton East B | | | 1804 | Brampton B | 1 | 1 | Dixie A | | |
| | 1805 | North Miss. | 7 | 0 | Milton | | | 1806 | Oakville B | 2 | 2 | Clarkson | | |
| | 1807 | Brampton East B | 1 | 1 | Brampton B | | | 1808 | Dixie B | 0 | 4 | Oakville B | | |
| | 1809 | Clarkson | 2 | 2 | Barrie | | | 1810 | Dixie A | 0 | 3 | North Miss. | | |
| | 1812 | North Miss. | 6 | 1 | Brampton East B | | | 1813 | Brampton B | 0 | 4 | Clarkson | | |
| | 1814 | Milton | 0 | 5 | Dixie A | | | 1815 | Barrie | 3 | 0 | Dixie B | | |
| | 1817 | Clarkson | 1 | 2 | North Miss. | | | 1818 | Brampton East B | 1 | 0 | Milton | | |
| | 1819 | Oakville B | 2 | 0 | Barrie | | | 1821 | Dixie B | 3 | 8 | Brampton B | | |
| | 1822 | Dixie A | 1 | 2 | Brampton East B | | | 1823 | North Miss. | 7 | 1 | Dixie B | | |
| | 1824 | Brampton B | 3 | 1 | Oakville B | | | 1825 | Milton | 1 | 5 | Clarkson | | |
| | 1828 | Clarkson | 3 | 0 | Dixie A | | | 1829 | Oakville B | 0 | 5 | North Miss. | | |
| | 1830 | Barrie | 4 | 1 | Brampton B | | | 1831 | Dixie B | 2 | 0 | Milton | | |
| | 1832 | Clarkson | 5 | 2 | Brampton East B | | | 1834 | Barrie | 0 | 1 | North Miss. | | |
| | 1835 | Oakville B | 10 | 0 | Milton | | | 1836 | Dixie B | 3 | 2 | Dixie A | | |
| | 1837 | North Miss. | 5 | 1 | Brampton B | | | 1838 | Milton | 0 | 2 | Barrie | | |
| | 1840 | Dixie A | 1 | 3 | Oakville B | | | 1841 | Brampton East B | 3 | 2 | Dixie B | | |
| | 1842 | Dixie B | 0 | 2 | Clarkson | | | 1843 | Oakville B | 6 | 2 | Brampton East B | | |
| | 1844 | Barrie | 1 | 0 | Dixie A | | | 1845 | Brampton B | 4 | 0 | Milton | | |
| | 1847 | Dixie A | 1 | 2 | Brampton B | | | 1848 | Milton | 0 | 10 | North Miss. | | |
| | 1849 | Clarkson | 4 | 2 | Oakville B | | | 1850 | Brampton East B | 1 | 0 | Barrie | | |
| | 1853 | Oakville B | 2 | 1 | Dixie B | | | 1854 | Barrie | 2 | 4 | Clarkson | | |
| | 1855 | North Miss. | 5 | 1 | Dixie A | | | 1856 | Brampton B | 4 | 3 | Brampton East B | | |
| | 1858 | Brampton East B | 0 | 5 | North Miss. | | | 1859 | Clarkson | 5 | 1 | Brampton B | | |
| | 1860 | Dixie B | 1 | 3 | Barrie | | | 1861 | Dixie A | 1 | 0 | Milton | | |
| | 1862 | Brampton B | 1 | 0 | Dixie B | | | 1863 | Milton | 0 | 3 | Brampton East B | | |
| | 1864 | North Miss. | 2 | 0 | Clarkson | | | 1865 | Barrie | 0 | 2 | Oakville B | | |
| | 1867 | Dixie B | 1 | 5 | North Miss. | | | 1869 | Clarkson | 8 | 0 | Milton | | |
| | 1870 | Oakville B | 3 | 4 | Brampton B | | | 1871 | Brampton East B | 1 | 2 | Dixie A | | |