THE GRAY TROPHY
(Presented by RS and CRW Gray)
PAST WINNERS
| 2010/11 | Newport AFC | ||
| 2009/10 | SS Peter & Paul | 2008/09 | Bank Street Athletic |
| 2007/08 | Menzieshill Athletic | 2006/07 | Arbroath HSFP |
| 2005/06 | Morgan Academy FP | 2004/05 | Dundee Shamrock |
| 2003/04 | Invergowrie | 2002/03 | Carnoustie YM |
| 2001/02 | Dee Club | 2000/01 | Arbroath HSFP |
| 1999/00 | Arbroath HSFP | 1998/99 | Dee Club |
| 1997/98 | Fintry Thistle | 1996/97 | Letham Lads Club |
| 1995/96 | Broughty United | 1994/95 | Dundee YMCA |
| 1993/94 | Dundee YMCA | 1992/93 | Letham Lads Club |
| 1991/92 | Kingsway Athletic | 1990/91 | Timex |
| 1989/90 | Riverside Athletic | 1988/89 | Riverside Athletic |
| 1987/88 | NCR | 1986/87 | Lawside Academy FP |
| 1985/86 | Riverside Athletic | 1984/85 | Kingsway TC |
| 1983/84 | Kingsway TC | 1982/83 | Harris Acadmey FP |
| 1981/82 | Timex | 1980/81 | Harris Acadmey FP |
| 1979/80 | Timex | 1978/79 | SMT |
| 1977/78 | Tayport | 1976/77 | SMT |
| 1975/76 | Auchterhouse | 1974/75 | NCR |
| 1973/74 | Broughty United | 1972/73 | SMT |
| 1971/72 | Grove Amateurs | 1970/71 | Lawside Academy FP |
| 1969/70 | NCR | 1968/69 |
Lawside Academy FP |
| 1967/68 | Lawside Academy FP | 1966/67 |
No competition |
| 1965/66 | NCR | 1964/65 |
NCR |
| 1963/64 | NCR | 1962/63 |
No competition |
| 1961/62 | Longforgan | 1960/61 |
Grays United |
| 1959/60 | Morgan Academy FP | 1958/59 |
Wormit Amateurs |
| 1957/58 | YM Anchorage | 1956/57 |
YM Anchorage |
| 1955/56 | RAY Leuchars | 1954/55 |
Invergowrie |
| 1953/54 | Wormit | 1952/53 |
Alyth Violet |
| 1951/52 | Tayport Violet | 1950/51 |
Tayport Violet |
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