It looked like the Shield was heading to the Bay of Plenty when Steamers winger Onisi Ratave converted a try, giving them a 33-30 lead with three minutes left on the clock.
However, a last-minute penalty saw Hawke's Bay first-five Tiaan Falcon level the scores and take the game to golden point extra time.
In extra time, Falcon stepped up again to nail a 35m penalty and retain the Shield with a 36-33 victory.
Drabble said he could not remember a Ranfurly Shield match ever being decided in extra time before.
"There was a bit of confusion about whether the Shield was still on the line in extra time, they had to check the rules. It has to rank near the top of the Shield challenges I've seen.
"We should never have got to that stage once we scored that try and converted it. All they had to do was hold on but they kicked the ball away.
"We scored five tries but gave away five penalty goals and they took the points. There were times where I just don't think we looked urgent enough."
In 1996, he was at Eden Park when Auckland produced an outrageous comeback to break Bay of Plenty hearts in a Ranfurly Shield challenge.
Having never won the Shield at that point, the Steamers led 29-11 with eight minutes left on the clock. Auckland piled on the pressure and the points, but with time virtually up remained a converted try from victory.
Then the Bay conceded a penalty and Matt Carrington - a product of Bay of Plenty - scored in the corner. He converted his try from the sideline and Auckland won 30–29.
"I still play the Eden Park clock for that," Drabble said.
"The clock just wasn't ticking down and the bloody ref was faulty too. We should've won it that day, it was bloody disappointing."
Drabble was at Eden Park again in 2004 when, finally, Bay of Plenty lifted the Ranfurly Shield for the first time in their history.
Glen Jackson was in superb form as the Steamers took a 20–15 half-time lead, and his match haul of 23 points proved decisive in the 33–28 victory over Auckland.
Wayne Ormond became the first Bay of Plenty captain to lift the Shield in front of the hundreds of fans who had travelled from all over the Bay of Plenty to watch the match.
"That was a great day, it really was," Drabble said.
"There's always a bit of a buzz when you have a Shield challenge and in 2004 it actually happened. They were parading from the moment they left the park, there were supporters everywhere. In that two weeks that they had the Shield they took it everywhere in the Bay of Plenty.
"I watched us defend it against Waikato a week later and then we lost it to Canterbury. I'll never forget, Justin Marshall scored the winning try and he crawled over the goal line."
Steamers head coach Daryl Gibson knows just how special the Ranfurly Shield is - he won it twice as Canterbury captain during his own playing career.
Speaking the day after Sunday's loss, he said his side was still hurting.
"To have come so close, to have victory within our control, and to let it slip in the dying seconds - we're still doing a bit of soul-searching," he said.
"We'll pick ourselves up, we came out of that game with two bonus points and reaffirmed we're a competitive team in this competition.
"I've won and lost the Shield so I understand the meaning of it. It was an exciting game yesterday, and I think for the neutral it would've been magnificent."
Gibson said despite the loss he was pleased with the performance his side produced following the Covid-19 lockdown disruption.
"I think all the teams acquitted themselves really well at the weekend. Teams played positively in all the games and tried to shift the ball.
"Any time you lose it exposes the gaps. There are plenty of work-ons there around some elements of our defence and our contact area.
"There are some parts of our attack that just need tidying up as well."
This weekend, the Steamers host Taranaki at the Tauranga Domain at 4.35pm on Sunday.