| Illawara Champions | ||||||
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| Second Division | ||||||
| Year | Grand Final Winners | Losing Finalists | Score | Minor Premiers | Runners-Up | Third Placed |
| 1977 | Wollongong United | Wollongong United | ||||
| 1978 | Lysaghts | Lysaghts | ||||
| 1979 | Warilla Sports | Crown United | ||||
| 1980 | Transkembla | Transkembla | ||||
| 1981 | Balgownie Rangers | Aris Wollongong | ||||
| 1982 | Wollongong Olympic | Wollongong Olympic | ||||
| 1983 | Coledale United | Coledale United | ||||
| 1984 | Unanderra Hearts | Unanderra Hearts | ||||
| 1985 | South Coast Croatia | Picton Rangers | ||||
| 1986 | All Stars | All Stars | ||||
| 1987 | Portside | Dapto | 2:1 | Illawarra Pelister | ||
| 1988 | Dapto | Ruse | 4:1 | Dapto | ||
| 1989 | Serbia United | Serbia United | Picton Rangers | Kiama | ||
| 1990 | Albion Park | Berkeley | Berkeley | Albion Park | Kiama | |
| 1991 | Russell Vale Lions | Westderra Hearts | 2:0 | Westderra Hearts | Russell Vale Lions | Kemblawarra |
| 1992 | Tarrawanna | Tarrawanna | South Coast Croatia | Kemblawarra | ||
| 1993 | Shoalhaven City | Kemblawarra | Shoalhaven City | Kiama | ||
| 1994 | Kiama | Woonona | 2:0 | Dapto | Kiama | Woonona |
| 1995 | Warrawong Barbarians | Warrawong Barbarians | Bellambi | Illawarra United | ||
| 1996 | Warilla Wanderers | Woonona | Warilla Wanderers | Berkeley | ||
| Not played after 1996 | ||||||
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