DIVISION TWO
PAST CHAMPIONS
| 2007/08 | Bank Street Athletic | 2006/07 | Elmwood AFC |
| 2005/06 | St James | 2004/05 | Douglas Sports Club |
| 2003/04 | Arbroath HSFP | 2002/03 | Inchture Athletic |
| 2001/02 | Carnoustie Y.M | 2000/01 | Dundee Shamrock |
| 1999/00 | Morgan Academy F.P. | 1998/99 | Michelin Athletic |
| 1997/98 | Carnoustie Y.M.H.S. | 1996/97 | Lochee United |
| 1995/96 | Dundee West | 1994/95 | Douglas Amateurs |
| 1993/94 | Fintry Thistle | 1992/93 | Inchture Athletic |
| 1991/92 | Letham Lads Club | 1990/91 | Kingsway Athletic |
| 1989/90 | Broughty United | 1988/89 | Monifieth Tayside |
| 1987/88 | St Francis | 1986/87 | Logie Harp |
| 1985/86 | Longforgan | 1984/85 | Lawside F.P. |
| 1983/84 | Barnhill | 1982/83 | Broughty United |
| 1981/82 | Arbroath H.S.F.P. | 1980/81 | St James |
| 1979/80 | Dundee Y.M.C.A. | 1978/79 | Longforgan |
| 1977/78 | Timex | 1976/77 | Invergowrie |
| 1975/76 | Barnhill | 1974/75 | Carnoustie YM/HS |
| 1973/74 | Invergowrie | 1972/73 | Kelso |
| 1971/72 | Auchterhouse | 1970/71 | Dundee Y.M.C.A. |
| 1969/70 | Carnoustie YM/HS | 1968/69 | Tayport |
| 1967/68 | Y.M.Anchorage | 1966/67 | Invergowrie |
| 1965/66 | Monifieth Tayside | 1964/65 | Lawside F.P. |
| 1963/64 | Monifieth Tayside | 1962/63 | Grove Academy F.P. |
| 1961/62 | Auchterhouse | 1960/61 | Craigiebank |
| 1959/60 | Harris Academy F.P. | 1958/59 | Timex |
| 1957/58 | Broughty United | 1956/57 | Craigiebank |
| 1955/56 | Bullionfield | 1954/55 | Morgan Academy F.P. |
| 1953/54 | Craigie Amateurs | 1952/53 | Lawside F.P. |
| 1951/52 | Balgay Amateurs | 1950/51 | Tayport Violet |
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