After a quiet opening quarter of an hour with no attempt at goal in the first 10 minutes of the match, the stiffest of deadlocks was broken by Dominic Solanke.
The former Bournemouth man was the only player following in after Pedro Porro’s long-range piledriver, and he was duly rewarded when Altay Bayindır’s weak parry allowed him to drill home the opener on the half-volley.
The remainder of the first half was an even affair as neither team were able to impose themselves on the game, although Christian Eriksen excelled for the visitors, and the former Spurs midfielder had United’s first shot on goal when his effort was blocked by Yves Bissouma.
History repeated itself on the stroke of half-time, as Eriksen once again got on the end of a Diego Dalot cutback, only for his goalward shot to once again be blocked.
Tottenham’s best spell of the first half came as Dejan Kulusevski saw more of the ball, with the Swede dancing beyond Bruno Fernandes to create an opportunity, only to see his strike from a narrow angle saved by Bayindır.
Ruben Amorim cut a frustrated figure when he emerged from the tunnel for the second half, and he had barely taken his place in the dugout by the time his team conceded for a second time.
Once again Spurs took advantage of loose Manchester United play, as Lisandro Martinez’s feeble clearance from James Maddison’s cross left Kulusevski with a simple finish to double his team’s advantage.
In response, the away side readied Joshua Zirkzee, Kobbie Mainoo, and derby hero Amad Diallo to enter the fray, but before the trio could get on the pitch, Spurs had grabbed a third and seemed to have put the outcome beyond doubt.
Having raced onto a Djed Spence ball over the top of the Red Devils’ defence, Solanke found himself a sight at goal and drilled the ball low beyond Bayindır.
What should have been a comfortable half-hour for Spurs descended into farce, as Fraser Forster’s horror show gifted United two goals.
The goalkeeper’s nightmare started when his wayward pass allowed Fernandes to square it to Zirkzee to tap into an empty net, and seven minutes later Forster dallied on the ball with Diallo bearing down on him, with the attempted clearance rebounding off the Ivorian and into the back of the net.
As the clock ticked down, Son Heung-min looked to have killed off United’s hopes thanks to yet another goalkeeping error, as the Korean’s corner sailed over Bayındır and directly into the goal, and they would hang on for the win despite Jonny Evans' late header from a corner.