| 24-25 | |  Frank Foyston (F) | 1891 | Minesing, ON, CAN | - |
| 24-25 | | Wally Elmer (F) | 1898 | Kingston, ON, CAN | - |
| 16-17 | | Frank Foyston (F) | 1891 | Minesing, ON, CAN | - |
| 15-16 | | Amos Arbour (F) | 1895 | Waubaushene, ON, CAN | - |
| 15-16 | | Jack Fournier (F) | 1892 | Ottawa, ON, CAN | - |
| 14-15 | |  Silas Griffis (D) | 1883 | Onaga, KS, USA | - |
| 14-15 | Stanley Cup was a challenge cup | Frederick Wellington Taylor (F) | 1884 | Tara, ON, CAN | - |
| 13-14 | | Henry Corbeau (D) | 1885 | Penetanguishene, ON, CAN | - |
| 13-14 | | Frank Foyston (F) | 1891 | Minesing, ON, CAN | - |
| 12-13 | | Jeff Malone (D) | 1888 | Québec, QC, CAN | - |
| 12-13 | | Joe Malone (F) | 1890 | Québec, QC, CAN | - |
| 11-12 | | Joe Hall (D) | 1882 | Staffordshire, GBR | - |
| 11-12 | | Joe Malone (F) | 1890 | Québec, QC, CAN | - |
| 11-12 | | Jack Grannary (F) | 1884 | Montréal, QC, CAN | - |
| 11-12 | | George Leonard (F) | 1886 | Québec, QC, CAN | - |
| 10-11 | | Bruce Ridpath (F) | 1884 | Lakefield, ON, CAN | - |
| 10-11 | | Alex Currie (F) | 1891 | Ottawa, ON, CAN | - |
| 08-09 | Stanley Cup was a challenge cup | Frederick Wellington Taylor (F) | 1884 | Tara, ON, CAN | - |
| 06-07 | | Silas Griffis (D) | 1883 | Onaga, KS, USA | - |
| 06-07 | | Billy McGimsie (F) | 1880 | Woodville, ON, CAN | - |
| 04-05 | | Angus Allen (D) | 1881 | Cornwall, ON, CAN | - |
| 04-05 | | Horace Gaul (F) | 1883 | Gaspé, QC, CAN | - |
| 03-04 | | James McGee (F) | 1879 | Ottawa, ON, CAN | - |
| 02-03 | | Rod Flett (D) | 1873 | Kildonan, MB, CAN | - |
| 02-03 | | Cecil Blachford (F) | 1880 | Montréal, QC, CAN | - |
| 01-02 | | Rod Flett (D) | 1873 | Kildonan, MB, CAN | - |
| 00-01 | | Billy Bawlf (F) | 1881 | Winnipeg, MB, CAN | - |