Reckon a few ky boys would be a chance of having 4? Reeves, Holman, Morris, Childs ??Without checking I would guess Shepparton have won the most senior premierships. As for players, Seymour won three in a row, someone from your mob maybe? United?
Nope. Just perused the website and Shepparton won 6 flags in 7 years in the 60's so that answers the question. In contemporary times I doubt it is more than 3 flags. Could easily be wrong though.