The Campbelltown Council flag flew proudly on a flag pole in front of Camden Council Chambers on Friday, July 3.
Both councils hold a friendly bet that the losing council in the Macarthur Football Association's annual City vs Country would fly would fly the winning council's flag.
City won this year's event for the first time with convincing 4-2 and 4-0 wins in the women's and men's games respectively.
Campbelltown mayor Paul Lake said "it felt fantastic" to finally achieve victory over Camden.
"It was a great night and everyone enjoyed the evening," he said.
"[Camden mayor] Lara Symkowiak took it in good spirit."
Cr Symkowiak said the country side enjoyed a good five year run as victors and it was great to be a part of the event.
Camden Council will host a reception for the winners at the Camden Civic Centre on July 22.
Mr Lake said: "Hopefully next year we can [win again and] fly our flag at the new Camden Council building at Oran Park."