A Tom Jackson brace has ended Auckland City's unbeaten run at 28 matches and handed Team Wellington the ASB Premiership title.
Jackson scored a stunning long range effort to open the scoring early in the second half of normal time, then sealed the deal in extra time with a superb headed goal.
Auckland City came into the match as huge favourites, their ability to boss possession and pick apart opponents earning them that right.
A brace from Tom Jackson has handed Team Wellington the ASB Premiership title.
But Team Wellington were able to get in the faces of the Auckland City midfield and prevent them from taking control of the game in a manner they would have liked.
It took 120 minutes for Team Wellington to really take control of the match, although if it weren't for a controversial penalty they may have won in normal time.
Sitting 2-2 after normal time, Ben Harris gave Team Wellington the lead minutes into the first period of extra time with a close range volley.
Auckland City goalkeeper Diego Rivas went up to try and collect a looping header but failed to grasp the ball, allowing it to bounce into the path of Wellington's potent striker.
Jackson then worked his second piece of magic for the game, securing the ASB Premiership trophy and a spot in the O League for Team Wellington.
At the start of the match it was Auckland City looking the better of the two teams.
Under pressure from Auckland's pressing, Team Wellington often put aimless passes upfield which were easily intercepted, launching quick counter-attacks.
The hosts were more secure on the ball, holding possession well and dictating terms.
But the old adage of 'if in doubt, kick it out' appeared to be working for Team Wellington as their defensive clearances led to a few chances and several corners.
Those corners showed how nervous Auckland City 'keeper Rivas looked, showing a lack of command for his area which would have had his centre backs nervous.
Where Auckland City dominated in the first 25 minutes, Team Wellington came into their own in the next 20 as the midfield calmed down on the ball and started to unlock the defence.
After the break Team Wellington stunned Auckland City with the first goal of the game, courtesy of Tom Jackson.
When Emiliano Tade lost control of a bouncing ball about 40 yards from goal, Jackson robbed him of the ball, took a few strides and smashed the ball beyond 'keeper Rivas with a wicked strike.
That gave Team Wellington a good spark, and their energy made it hard for Auckland City to retain possession like they had throughout that opening 25 minutes.
Spark turned to clear rage moments later when Auckland City were awarded a penalty.
Team Wellington failed to clear a tame cross, allowing it to bounce between several players when a thumping clearance clattered into a defenders hand from close distance.
Matt Conger had no hesitation in blowing his whistle, although on reflection he may grow to find the ruling was harsh.
Joao Moreira drilled the spot kick down the middle, past a diving Scott Basalaj, to equalise for Auckland City.
As anger levels grew, Team Wellington's defensive shape suffered with aggressive pressing allowing Auckland City more space on attack.
All of a sudden the ball movement and patient possession of the start of the match was back.
Aggression proved Team Wellington's undoing with 10 minutes to play. Harris brought down Auckland City defender Daewook Kim, then Kim headed home from the resulting freekick to make it 2-1.
But a magical turn from Harris into the box led Takuya Iwata to foul inside the box, and Cole Peverley stepped up to equalise for Team Wellington from the spot and send the match to extra time.