Harry Kane scored his ninth goal in six games for Tottenham as Mauricio Pochettino’s side won 1-0 at Qarabag to reach the last 32 of the Europa League.
The England striker, a surprise inclusion in the starting line-up with Spurs facing Premier League champions Chelsea less than 72 hours later, nodded in the winner with 12 minutes remaining of the Group J tie in Baku
It meant Tottenham’s longest-ever journey for a competitive fixture – a 5,000-mile round trip to the capital of Azerbaijan – proved worthwhile as they made the last 32 with a match to spare.
What was shaping up to be a frustrating evening, with both Son Heung-min and Dele Alli denied by the woodwork, was finally settled by in-form Kane’s ninth goal in six games.
Played in front of a boisterous partisan crowd, and with barely 100 visiting fans in attendance, Tottenham’s first chance fell to England new boy Alli.
But unfortunately the midfielder could not repeat his Wembley stunner against France when meeting Kieran Tripper’s cut-back and scuffed his shot wide.
Son and Toby Alderweireld had deflected efforts saved by Ibrahim Sehic before Alli headed Christian Eriksen’s corner into the arms of the Qarabag goalkeeper.
Kane endured a tough first half with Tottenham’s final ball repeatedly failing to reach him, although he did hit a snap-shot from the edge of the area which had Sehic scrambling as it flew narrowly wide.
The hosts were intent on sitting deep and keeping men behind the ball, but they spurned a glorious in first-half stoppage time when a two-against-one break ended with Dani Quintana firing too close to Hugo Lloris.
That let-off seemed to give Spurs a lift and moments after the interval Eriksen let fly with a shot which just missed the target.
Qarabag were still proving to be a nuisance on the counter, though, and Quintana saw one curling effort shot deflected wide before forcing a decent save from Lloris with a 20-yard drive.
Tottenham probed for a winner and Alli’s shot from Kane’s inside pass was repelled by Sehic before, on the hour mark, Son unleashed a cracker from the edge of the box which clattered off the crossbar.
Ten minutes later Alderweireld’s ball over the top found Alli at the far post but his volley came back off the foot of Sehic’s right-hand post.
But moments later Kane made the breakthrough, after Son flicked on Eriksen’s corner, the England striker getting the final touch to nod the ball over the line and ensure Tottenham’s European adventure continued into 2016.