An astonishing finish saw Scotland come from behind and go ahead with only minutes remaining thanks to two Leigh Griffiths penalties before Harry Kane grabbed a late equaliser to ensure England remained undefeated in qualifiers since 2009.
Scotland hold firm against captain Kane threat
As expected with such a rivalry, there was a feisty opening to proceedings, optimised by Scott Brown stamping his authority on the game with a rash challenge that earned him a booking inside three minutes. Scotland's aggressive outset put them on top of the game but they struggled to make any chances of note before the contest settled down midway through the first half and surprise starter Jake Livermore began to see more of the ball.
Despite getting on top of possession, England were often too predictable and when chances finally fell to captain Harry Kane he could not take them. The Premier League Golden Boot winner fired over from Eric Dier's diagonal pass and then mishit an effort from two yards when played in by Adam Lallana. Kane actually went closest from all of 30 yards only to see his goalbound effort cleared off the line by Kieran Tierney.
A sparky opening had filtered out throughout the first 45 minutes apart from Kane's chances. However, England ended the half well with Lallana hitting the side netting after nifty footwork and Livermore forcing Craig Gordon into a smart stop.
Super-sub Oxlade-Chamberlain steals an opener for the visitors
The visitors looked to pick up where they left off and Livermore slashed an effort at Scotland left wing-back Andrew Robertson with the ball rebounding off the defender and hitting the post. The ball pinged around the penalty area but no England player could find a telling touch from the ensuing scramble.
Chris Smalling and Gary Cahill had looked somewhat nervy throughout in the centre of England's defence and a lack of judgement from the pair allowed Robertson a chance on the edge of the box but he slashed his strike wide after venturing forward. Scotland used that opportunity to surge into their opponent's half, buoyed on by a rejuvenated home crowd, as England found themselves on the ropes. Yet the hosts' lack of creativity showed as they were subjected to distant efforts.
The visitors needed a new spark and they got it within five minutes of Oxlade-Chamberlain replacing Marcus Rashford on the right-wing. A stroke of fortune allowed him to start a run that took him past three defenders before releasing an effort. Gordon completely misjudged his position and saw the ball float past him as England took a vital lead.
Griffiths double thwarted by late Kane equaliser in astonishing finish
Oxlade-Chamberlain almost turned provider moments later when he clipped the ball to the back post only for Lallana to nod over with space around him.
Yet Scotland are a spirited nation and they continued to dig deep. A handful of long-range efforts went begging before Leigh Griffiths was granted a set-piece opportunity when Cahill clattered into substitute Ryan Fraser. Despite a wretched time in front of goal for his nation after failing to net in 12 previous matches, the striker stepped up to curl a beauty past Joe Hart to draw Scotland level. Cue pandemonium.
Scotland were a revived unit and continued to drive forward. When Chris Martin won a free-kick in a similar position after being taken down by Livermore, Hampden Park prayed for deja-vu. Griffiths delivered. This time curling the ball the other side of Hart, Scotland fans were cast into delirium.
The contest looked as good as over as the game drifted into injury time. Dier hit a free-kick straight at Gordon before England worked the ball out wide to Raheem Sterling. The substitute curled an incredible pass between Scotland's back three and Kane drifted in to stab home in the third of four added on minutes. Cue silence.
The remarkable finish leaves England still comfortably in charge of the group but Scotland still with a lot of work to do if they want to spend next summer in Russia. Could these final moments be pivotal to both nations' hopes of World Cup 2018 qualification?