Everton suffered their first defeat since early October as Tottenham came from behind to edge the Blues at White Hart Lane.
Roberto Martinez's men were looking to stretch an unbeaten run of eight games by ending a winless spell away at Spurs that began exactly six years ago to the day.
They got off to the perfect start when the masterful Kevin Mirallas - so influential in his three games since returning from injury just eight days ago - curled home a breathtaking opener from 20 yards.
However, Tottenham hit back to lead at the break, well-taken goals from Christian Eriksen and Roberto Soldado ultimately proving enough to move Mauricio Pochettino's men above the Blues, who drop to 10th in the Barclays Premier League table.
Martinez was able to welcome back Leighton Baines and Gareth Barry from hamstring and ankle injuries respectively, the duo having both missed Everton's last two games.
The pair returned as two of four changes from Thursday's 2-0 win over Wolfsburg, with Ross Barkley and Seamus Coleman also restored to the starting line-up.
And it was Barkley who almost inspired an early Blues opener. Setting off on a mazy dribble, the youngster worked himself some space 20-yards out but saw his shot - in an almost carbon copy repeat of last Saturday's first goal against West Ham - bobble into the path of Romelu Lukaku.
This time, however, the Belgian failed to get hold of his first-time shot, allowing Hugo Lloris to save with his legs.
On 15 minutes, his compatriot had no such problems. A lofted ball into the box was headed clear by Ryan Mason but Mirallas beat Soldado to it as it bounced, then wrong-footed the Spaniard and exquisitely curled his shot high into Lloris' top-left corner. A stunner.
There must be something about White Hart Lane for the winger. His strike here two years' ago - a solo run and finish rather than a belting strike - was equally as special. Pick your own favourite.
Rattled, Spurs almost gifted the Blues a chance at a second four minutes later but Lloris marginally beat Lukaku to Vlad Chiriches' lightweight pass back.
As it was, the hosts went up the other end just two minutes later and made it level. Kane's initial shot from the edge of the box was palmed away by Howard but Eriksen got to the loose ball and craftily dinked it back past the American and the covering Barry into the bottom corner.
Undoubtedly boosted by the Dane's strike, Tottenham suddenly had a new impetus. Kane fired over from edge of box on 28 minutes, then worked his way through the heart of Everton's midfield moments later only to shot tamely at Howard from a similar position. Eriksen, too, went too close for comfort with a deflected shot that crept wide of the post.
At the other end, Coleman's low drive from the right was easily dealt with by Lloris but there was little else before the break.
Ruefully, the same could not be said for Spurs. Deep into just one minute of added time, Aaron Lennon poked the ball past Sylvain Distin, into the path of Soldado and the striker bided his time before picking his spot past Howard.
The tide continued to roll with the hosts after the interval and on 54 minutes Howard had to be alert to catch a long-range effort from Kane.
Three minutes later the American was grateful when Federico Fazio - six-yards out - failed to connect with Eriksson's driven right-wing cross.
And when Ryan Mason fired over with a rising piledriver soon after, Martinez decided it was time for a change.
Samuel Eto'o and goalscorer Mirallas were withdrawn, with Leon Osman and Aiden McGeady given half-an-hour to help force a route back into the contest.
Yet, not since THAT Wimbledon game in 1994 have Everton come from 2-1 down at half-time to win a game. Here their efforts wouldn't even be rewarded with an equaliser.
The closest the Blues came was on 71 minutes when Barkley's eye spotted Coleman in space. The pass put his teammate one-on-one with Lloris but the Frenchman was panther-like off his line to spread himself and deflect the right-back's effort behind for a corner.
A late Lukaku header also appeared to strike the hand of Fazio but referee Michael Oliver saw no infringement. That Besic got away with a trip on Kane in the opposite area moments later maybe levelled it out.
Everton's window for wound-licking is minimal. Martinez's men return to action against fourth-bottom Hull City at Goodison Park on Wednesday.