Then with Otago ahead by a solitary point with four minutes to go, Gregory conceded a penalty in front of the sticks and Taniwha all but kissed the game goodbye.
Prior to that indiscretion, Rene Ranger was penalised for harassing the Otago halfback in a ruck despite being warned three times by the referee.
The quality of the passes from Otago, spreading from flank to flank in the first spell, caught Northland off guard and they were not afraid to run from their 22m.
But Northland showed it's defensive prowess, twice stopping Otago's rolling maul near the tryline- a massive statement that the Taniwha were no pushovers.
Halfback Sam Nock holding up Josh Ioane on the Taniwha tryline would have had a massive influence on the outcome, had Northland found the composure to close out the match in the end.
Centre Tamati Tua scored Northland's first try in the corner after a well-timed pass from fullback Matty Wright off set piece play.
The visitors got off to a flying start in the second half when first five-eighth Jack Debreczeni stretched and planted the ball on the goal line while his team were under advantage.
With Ranger loitering behind him, Debreczeni fielded a pass off a ruck, wriggled his way past three defenders before scoring.
Northland realised if they could gain a yard at a time and continue chipping away, they could force Otago to chase the match. But as soon as it all begin, it unravelled.
Isileli Tu'ungafasi's dangerous tackle that netted Otago three points and Ranger knocking a pass from Debreczeni in the Taniwha 22m line gave the hosts a lifeline- and a win.
Northland were perhaps guilty of overplaying the ball in the dying minutes.
Otago were rampant. Northland confused and desperate, unable to comprehend that a match so secure might now be wrenched from them.
The men in the Cambridge Blue were grouping, waiting and determined to claim the ball and mount a last-ditch effort to steal win.
But the Otago boys bore down upon them like a military charge from which there would be no survivors
There isn't a miracle cure for Northland and it may take some time yet before they finally build the collective skills, experience, maturity and tactical certainty to win regularly.
Northland are now fifth in the seven team Championship division with 6 points. The Taniwha's next game is at home in Whangārei against Manawatu on Friday, from 5.45pm.
Scorers:
Otago 27 (Dylan Nel, Jona Nareki, Joketani Koroi tries, Josh Ioane 3 con, 2 pen) Northland 23 (Tamati Tua tries, Jack Debreczeni try, 3 pen, 2 con). HT: 7-10.