Bentleigh Greens have upset Wellington Phoenix 1-0 to become the sixth state-league side in FFA Cup history to beat an A-League opponent.
The Greens took the lead midway through the first half and had a man sent off 10 minutes later but were still able to hold out their A-League opponents to secure a famous victory at Kingston Heath on Tuesday night.
It is just the sixth time an A-League side has been beaten in the cup by a team outside of the national competition.
Rudan was coaching the Phoenix in his first competitive match and fielded a strong starting team featuring former Socceroos Nathan Burns and Mitch Nichols, Fijian star Roy Krishna and new recruit Steven Taylor, an ex-Premier League player for Newcastle United.
Yet there was little discernible difference between themselves and Victorian NPL powerhouse Bentleigh, who made the FFA Cup semi-finals in 2014.
Marco Jankovic, the son of former Real Madrid defender Milan Jankovic, put the Greens in front with a header from a corner kick in the 23rd minute.
Soon after, James Kelly was shown his second yellow card and sent off following a late challenge on another new Wellington signing Michal Kopczynski.
But the Phoenix did not have the quality in the final third to break down a resolute Bentleigh defence.
Newcastle Jets had no such troubles at Cbus Super Stadium, beating a plucky Gold Coast Knights 1-0 courtesy of an early Nikolai Topor-Stanley goal.
The Jets had flown straight to the Gold Coast from their pre-season camp in Spain, shrugging off the effects of jetlag to finally register their maiden FFA Cup win in the tournament's five-year history.
Devonport Strikers are also into the round of 16 for the second time after upsetting Northcote City 3-1 in Melbourne, becoming the first Tasmanian team to win an FFA Cup match on the road.