LEAGUE DIVISION ONE
PAST CHAMPIONS
| 2009/10 | SS Peter & Paul | 2008/09 | Bank Street Athletic |
| 2007/08 | Elmwood AFC | 2006/07 | St James AFC |
| 2005/06 | Dundee University | 2004/05 | Barnhill |
| 2003/04 | Letham Lads Club | 2002/03 | Carnoustie YM |
| 2001/02 | Dee Club | 2000/01 | Kelso |
| 1999/00 | Dundee YMCA | 1998/99 | Dundee College |
| 1997/98 | Newport | 1996/97 | Broughty United |
| 1995/96 | Douglas Amateurs | 1994/95 | Morgan Academy FP |
| 1993/94 | Letham Lads Club | 1992/93 | Barnhill |
| 1991/92 | Kingsway Athletic | 1990/91 | Arbroath HSFP |
| 1989/90 | Riverside Athletic | 1988/89 | Riverside Athletic |
| 1987/88 | Lawside FP | 1986/87 | Riverside Athletic |
| 1985/86 | Riverside Athletic | 1984/85 | Harris Academy FP |
| 1983/84 | Kingsway TC | 1982/83 | Harris Academy FP |
| 1981/82 | Tayport | 1980/81 | Harris Academy FP |
| 1979/80 | Harris Academy FP | 1978/79 | S. M. T. |
| 1977/78 | Auchterhouse | 1976/77 | Auchterhouse |
| 1975/76 | Auchterhouse | 1974/75 | Broughty United |
| 1973/74 | Broughty United | 1972/73 | Lawside FP |
| 1971/72 | Broughty United | 1970/71 | N. C. R. |
| 1969/70 | Broughty United | 1968/69 | N. C. R. |
| 1967/68 | N. C. R. | 1966/67 | N. C. R. |
| 1965/66 | N. C. R. | 1964/65 | N. C. R. |
| 1963/64 | N. C. R. | 1962/63 | N. C. R. |
| 1961/62 | N. C. R. | 1960/61 | N. C. R. |
| 1959/60 | N. C. R. | 1958/59 | YM Anchorage |
| 1957/58 | YM Anchorage | 1956/57 | Wormit |
| 1955/56 | Wormit | 1954/55 | YM Anchorage |
| 1953/54 | Invergowrie | 1952/53 | YM Anchorage |
| 1951/52 | YM Anchorage | 1950/51 | YM Anchorage |
| 1948/49 | YM Anchorage | 1947/48 | YM Anchorage |
| 1946/47 | YM Anchorage | 1940-46 | No Competition |
| 1939/40 | YM Anchorage | 1938/39 | YM Anchorage |
| 1937/38 | YM Anchorage | 1936/37 | YM Anchorage |
| 1935/36 | YM Anchorage | 1934/35 | YM Anchorage |
| 1933/34 | YM Anchorage | 1932/33 | R.A.F.Leuchars |
| 1931/32 | Clifton Thistle | 1930/31 | Aeros |
| 1929/30 | Aeros | 1928/29 | Grove Academy F.P. |
| 1927/28 | YM Anchorage | 1926/27 | Aeros |
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