The match ended 2-1, but Ryan’s side had led 1-0 until the final minute, when Anderlecht's Aleksandar Mitrovic levelled, driving home a shot from the edge of the box after Brugge’s Timmy Simons failed to clear a cross.
Ryan was visibly angered by the situation having kept his sheet clean until that point, and the match looked destined for a nervous period of extra-time.
But somehow, his team-mates rallied, and three minutes into added time, Israel international Lior Refaelov slotted home a winner to give Brugge its 11th cup triumph.
Victory was the least Ryan and his team-mates deserved. Brugge had earlier been denied a good shout for a penalty, and also saw two goals disallowed in quick succession in the second half, one for a foul on the keeper and another for offside, with replays suggesting both calls were incorrect.
Prior to scoring the dramatic late winner, Refaelov was also involved in the opening goal on 12 minutes, lofting a free-kick to the far post from the left touchline which Tom De Sutter volleyed home emphatically.
Ryan had a reasonably quiet game, other than one super save 15 minutes into the second half, tipping a Mitrovic header over the bar to maintain Brugge’s lead. He also made another good stop 10 minutes from time, but had no chance with Mitrovic's leveller.
That mattered little as Brugge secured the win, sparking wild celebrations from the team and fans.
The match had been delayed by 30 minutes after Anderlecht arrived late to the King Baudouin Stadium in Brussels owing to traffic. There was also crowd trouble in town as Brugge fans clashed with police, tearing up road signs and barricades to hurl at the officials.
Ryan now links up with the Socceroos for international friendlies against Germany and FYR Macedonia. He will then return to Brugge to help its campaign to lift the Belgian Pro League title.