| # | Day | Date | Home | Home | Away | Away | ||
|---|---|---|---|---|---|---|---|---|
| 1921 | Wed | May 21 | Darl U14B T1 | Darlington Rush U14B T1 | 3 | 1 | OTSC U14BT2 | Oshawa Turul Green U14B T2 |
| 1922 | Wed | May 21 | OTSC U14BT2 | Oshawa Turul White U14B T2 | 9 | 3 | KLSC U14BT2 | Kawartha Inferno U14B T2 |
| 1923 | Wed | May 21 | PCSC U14BT1 | Peterborough City Blue U14B T1 | 3 | 0 | PCSC U14BT2 | Peterborough City White U14B T2 |
| 1924 | Wed | May 21 | WFC U14BT1 | Whitby FC U14B T1 | 4 | 0 | NHSC U14BT2 | Northumberland U14B T2 |
| 1925 | Wed | May 28 | Darl U14B T1 | Darlington Rush U14B T1 | 1 | 1 | MLC U14BT1 | Cavan FC U14B T1 |
| 1926 | Wed | May 28 | NHSC U14BT2 | Northumberland U14B T2 | 2 | 3 | OTSC U14BT2 | Oshawa Turul White U14B T2 |
| 1927 | Wed | May 28 | OTSC U14BT2 | Oshawa Turul Green U14B T2 | 0 | 3 | PCSC U14BT1 | Peterborough City Blue U14B T1 |
| 1928 | Wed | May 28 | PCSC U14BT2 | Peterborough City White U14B T2 | 4 | 1 | KLSC U14BT2 | Kawartha Inferno U14B T2 |
| 1929 | Wed | Jun 4 | OTSC U14BT2 | Oshawa Turul White U14B T2 | 3 | 3 | Darl U14B T1 | Darlington Rush U14B T1 |
| 1930 | Wed | Jun 4 | MLC U14BT1 | Cavan FC U14B T1 | 2 | 5 | PCSC U14BT1 | Peterborough City Blue U14B T1 |
| 1932 | Wed | Jun 4 | WFC U14BT1 | Whitby FC U14B T1 | 4 | 0 | OTSC U14BT2 | Oshawa Turul Green U14B T2 |
| 1931 | Thu | Jun 5 | KLSC U14BT2 | Kawartha Inferno U14B T2 | 1 | 12 | NHSC U14BT2 | Northumberland U14B T2 |
| 1937 | Mon | Jun 9 | PCSC U14BT2 | Peterborough City White U14B T2 | 1 | 2 | Darl U14B T1 | Darlington Rush U14B T1 |
| 1933 | Wed | Jun 11 | Darl U14B T1 | Darlington Rush U14B T1 | 1 | 1 | WFC U14BT1 | Whitby FC U14B T1 |
| 1934 | Wed | Jun 11 | PCSC U14BT1 | Peterborough City Blue U14B T1 | 3 | 0 | NHSC U14BT2 | Northumberland U14B T2 |
| 1935 | Wed | Jun 11 | MLC U14BT1 | Cavan FC U14B T1 | 4 | 1 | OTSC U14BT2 | Oshawa Turul White U14B T2 |
| 1936 | Wed | Jun 11 | OTSC U14BT2 | Oshawa Turul Green U14B T2 | 4 | 0 | PCSC U14BT2 | Peterborough City White U14B T2 |
| 1938 | Wed | Jun 18 | OTSC U14BT2 | Oshawa Turul Green U14B T2 | 5 | 2 | OTSC U14BT2 | Oshawa Turul White U14B T2 |
| 1939 | Wed | Jun 18 | KLSC U14BT2 | Kawartha Inferno U14B T2 | 0 | 18 | WFC U14BT1 | Whitby FC U14B T1 |
| 1940 | Wed | Jun 18 | NHSC U14BT2 | Northumberland U14B T2 | 1 | 1 | MLC U14BT1 | Cavan FC U14B T1 |
| 1941 | Wed | Jul 2 | NHSC U14BT2 | Northumberland U14B T2 | 6 | 3 | OTSC U14BT2 | Oshawa Turul Green U14B T2 |
| 1942 | Wed | Jul 2 | KLSC U14BT2 | Kawartha Inferno U14B T2 | 0 | 18 | MLC U14BT1 | Cavan FC U14B T1 |
| 1943 | Wed | Jul 2 | PCSC U14BT1 | Peterborough City Blue U14B T1 | 2 | 2 | WFC U14BT1 | Whitby FC U14B T1 |
| 1944 | Wed | Jul 2 | OTSC U14BT2 | Oshawa Turul White U14B T2 | 3 | 1 | PCSC U14BT2 | Peterborough City White U14B T2 |
| 1945 | Wed | Jul 9 | NHSC U14BT2 | Northumberland U14B T2 | 2 | 2 | Darl U14B T1 | Darlington Rush U14B T1 |
| 1948 | Wed | Jul 9 | PCSC U14BT1 | Peterborough City Blue U14B T1 | 18 | 0 | KLSC U14BT2 | Kawartha Inferno U14B T2 |
| 1947 | Wed | Jul 9 | MLC U14BT1 | Cavan FC U14B T1 | 3 | 1 | OTSC U14BT2 | Oshawa Turul Green U14B T2 |
| 1946 | Wed | Jul 9 | WFC U14BT1 | Whitby FC U14B T1 | 7 | 1 | PCSC U14BT2 | Peterborough City White U14B T2 |
| 1949 | Wed | Jul 16 | PCSC U14BT2 | Peterborough City White U14B T2 | 0 | 4 | NHSC U14BT2 | Northumberland U14B T2 |
| 1950 | Wed | Jul 16 | KLSC U14BT2 | Kawartha Inferno U14B T2 | 2 | 10 | Darl U14B T1 | Darlington Rush U14B T1 |
| 1952 | Wed | Jul 16 | MLC U14BT1 | Cavan FC U14B T1 | 2 | 2 | WFC U14BT1 | Whitby FC U14B T1 |
| 1951 | Mon | Jul 21 | OTSC U14BT2 | Oshawa Turul White U14B T2 | 0 | 2 | PCSC U14BT1 | Peterborough City Blue U14B T1 |
| 1953 | Wed | Jul 23 | Darl U14B T1 | Darlington Rush U14B T1 | 0 | 7 | PCSC U14BT1 | Peterborough City Blue U14B T1 |
| 1954 | Wed | Jul 23 | OTSC U14BT2 | Oshawa Turul Green U14B T2 | 9 | 0 | KLSC U14BT2 | Kawartha Inferno U14B T2 |
| 1955 | Wed | Jul 23 | PCSC U14BT2 | Peterborough City White U14B T2 | 1 | 4 | MLC U14BT1 | Cavan FC U14B T1 |
| 1956 | Wed | Jul 23 | WFC U14BT1 | Whitby FC U14B T1 | 1 | 0 | OTSC U14BT2 | Oshawa Turul White U14B T2 |
| 2372 | Wed | Jul 30 | PCSC U14BT1 | Peterborough City Blue U14B T1 | 5 | 0 | MLC U14BT1 | Cavan FC U14B T1 |
| 2371 | Wed | Jul 30 | Darl U14B T1 | Darlington Rush U14B T1 | 0 | 6 | WFC U14BT1 | Whitby FC U14B T1 |
| 2373 | Wed | Aug 6 | WFC U14BT1 | Whitby FC U14B T1 | 2 | 2 | PCSC U14BT1 | Peterborough City Blue U14B T1 |
| 2374 | Wed | Aug 6 | MLC U14BT1 | Cavan FC U14B T1 | 1 | 1 | Darl U14B T1 | Darlington Rush U14B T1 |
