First-half goals from Sammie Szmodics and Liam Delap fired Ipswich to a first Premier League victory in 22 years as they stunned Tottenham with a superb 2-1 away win.
The promoted Tractor Boys had been denied a maiden league success this season by a stoppage-time leveller against Leicester last weekend, but finally got off the mark at the 11th attempt.
Szmodics’ acrobatic effort put Ipswich ahead in the 31st minute and Delap made it 2-0 12 minutes later to set Kieran McKenna’s side halfway towards a long-awaited result.
Rodrigo Bentancur reduced the deficit for Spurs with 69 minutes played, but they could not muster a grand finale and missed out on the chance to rise to third in the table.
Sammie Szmodics opens the scoring with an acrobatic effort (Steven Paston/PA)
Tottenham had won their previous six home matches, but were up against a manager that spent 16 years at the club as player and coach in McKenna.
Ex-Spurs academy coach McKenna almost had a goal to celebrate on the second minute of his return as Szmodics bundled his way into the penalty area and had a low shot saved by Guglielmo Vicario.
It sparked an end-to-end start as Brennan Johnson poked wide Son Heung-min’s cross soon after before Town defender Cameron Burgess headed against the crossbar from a Leif Davis corner.
The hosts responded with a Dominic Solanke shot deflected over and the England international forced Arijanet Muric into a decent save with a low 19th-minute effort after Cristian Romero’s ball over the top.
Ange Postecoglou’s team had appeared to be getting to grips with Ipswich’s aggressive press by the midway point of the first half as Muric made another stop to prevent an own goal from Davis after he deflected Johnson’s cross goalwards.
Rodrigo Bentancur (right) celebrates his second-half goal (Steven Paston/PA)
However, the visitors had already looked a threat out wide and made the breakthrough just after the half-hour mark through Szmodics.
Jens Cajuste’s cross was headed up in the air by Romero under pressure from Delap and Szmodics was first to the loose ball with a fine overhead kick which beat Vicario from close range.
Johnson had been slow to react and one goal for the visitors quickly become two after more excellent wing play.
As a Spurs move broke down with a poor Son pass, Omari Hutchinson carried the ball impressively and possession was worked out to Szmodics, whose cross was parried by Vicario into Radu Dragusin and it allowed Delap to lash home on the goal-line.
Boos greeted half-time, but Tottenham returned with renewed vigour and after the break with Son having a shot tipped over and Solanke bundling home from a corner only for VAR to cut short home celebrations as the England forward had handled the ball before it went in the net.
Ipswich manager Kieran McKenna celebrates victory after the final whistle (Steven Paston/PA)
Spurs remained in the ascendancy but were restricted to hopeful efforts as Solanke drilled over from long range before Son curled off target.
Postecoglou sent on Timo Werner with 24 minutes left and Tottenham did pull one back three minutes later through a set-piece.
Pedro Porro produced an inch-perfect corner to the near post, where Bentancur powered home a header for his first goal of the season.
Spurs peppered the Ipswich goal with another Son effort sent off target before Werner forced Muric to tip over his 25-yard strike.
Werner lifted another shot over before Postecoglou turned to James Maddison, but the Tractors Boys would not be denied and held on for a memorable win.