It took 120 minutes of play and 10 penalty shots to eventually declare Roslyn Wakari the winner and the team to advance to the third round of the national competition.
Keeper Tom Stevens emerged as a hero when deflecting Dunedin Tech's final shot in the match's penalty shoot-out to send his team-mates and their supporters in to raptures.
The 4-3 shootout result finally split the two teams who were tied 2-2 at the end of two halves of overtime and 1-1 at the end of regular time.
Roslyn Wakari took an early advantage in the second half of extra time after the two teams played out a goal-less first stanza.
Nick Treadwell slotted a header from a long range pass to put his team ahead within seconds of the teams returning to the pitch.
Technical had more than 13 minutes to level scores getting their best chance when Elliot Jenkins hit the turf heavily.
Tim McLennan could not slot the resulting penalty shot which was deflected by Tom Stevens, but on a second swipe the Tech player got the ball past the keeper to again level the scores.
The first half and the early part of the second half had static, defensive football with few legitimate shots on goal. Tech held a 1-0 advantage after Tim McLennan and Rhys Quarrell combined to score with some slick attacking play.
The goal came after some of the Roslyn Wakari players turned their focus to appealing to the referee for a possible penalty.
A 1-0 Tech win looked likely until a Roslyn equalised through a brilliant effort from Tennessee Kinghorn late in the second half of regular time.
Roslyn's penalty shoot-out win means it progresses to the next round of the Chatham Cup in three weeks.
Fellow Dunedin side Green Island also needed extra time to progress further in the national competition.
It beat Queenstown 1-0 after the teams were deadlocked at 0-0 at the end of regular time.
Mosgiel will also progress to the Chatham Cup's third round after it beat Northern at Forrester Park in Dunedin.
Grants Braes beat Old Boys 3-0 in Invercargill yesterday and it, too, progresses in the competition.
Meanwhile, Dunedin Technical did not let Roslyn Wakari edge it out in yesterday's round two matches of the Kate Sheppard Cup.
A lone Shontelle Smith-goal enabled Dunedin Tech to win 1-0 at Ellis Park in Dunedin yesterday.
A double from Otago University's Britney-Lee Nicholson helped her side beat Queenstown 3-2 at Logan Park in Dunedin yesterday.
Jamiee Paterson also landed a goal to help the winner progress to round three of the Kate Sheppard Cup in three weeks.
Amy Hislop scored two goals for Queenstown in their defeat.
