Ten-man Tottenham Hotspur were knocked out of the Europa League as Gent held them to a draw at a sell-out Wembley.
Spurs, who trailed 1-0 after the first leg of the last-32 tie, made a great start as Christian Eriksen slipped an angled shot under Gent keeper Lovre Kalinic.
The visitors equalised through Harry Kane’s own goal, leaving Spurs needing to score twice more in front of a Europa League record attendance of 80,465.
Their task became harder when midfielder Dele Alli was sent off shortly before half-time for a dangerous high tackle.
Victor Wanyama’s curler into the top-left corner revived Spurs’ hopes, only for substitute Jeremy Perbet to prod Gent into the last 16 with fewer than 10 minutes left.
Spurs’ elimination means they have only reached the Europa League quarter-finals once in the past six seasons.
Manchester United, who beat French side Saint-Etienne 4-0 on aggregate, will be the only British side in the last-16 draw on Friday (12:00 GMT).
Spurs pay price for Alli red card
Despite them needing to score at least twice as the match approached half-time, few would have written off Spurs.
But they were then reduced to 10 men after Alli’s poor tackle.
The 20-year-old England midfielder has previously shown glimpses of a fiery streak, alongside his technical brilliance, but this was the first red card of his career.
Alli felt referee Manuel de Sousa should have given him a free-kick close to the halfway line and briefly remonstrated with the Portuguese official before turning and launching into Genk midfielder Brecht Dejaegere with a studs-up challenge.
Alli caught Dejaegere just under his right knee – and luckily the Belgian appeared to escape serious injury.
Tottenham did not escape without damage, though.
Spurs’ European struggles continue
Tottenham, particularly since Mauricio Pochettino became manager, have often drawn praise for their fearless and confident approach, and they have become regular title challengers.
But it is a different story in Europe.
In truth, they should still have progressed despite Alli’s dismissal, only poor finishing costing them in a dominant performance against a team containing a man extra.
The blame largely lies in a lifeless performance in Belgium.
Gent’s first-leg victory was only their third win in 13 matches, with their recent form dropping them to eighth place in a Belgian top flight ranked as only the ninth-best European league.
Indeed Belgian leaders Club Brugge, the reigning champions, lost all six matches in their Champions League group, including a 3-0 home defeat and 2-1 loss against Leicester City.
While Tottenham’s deficiencies were clear, Gent deserve credit. They were organised, disciplined and clinical when their rare chances arrived.
Perbet, who scored the winner last week, put the tie beyond Spurs with the away team’s first shot on target at Wembley, sparking exuberant scenes among the 10,000 visiting fans.
Tottenham manager Mauricio Pochettino:
“I am very disappointed. Once again we were excited to play today in front of our fans. We started well and scored. The tie was open but we conceded a goal in one action in the first half. After that it was complicated.
“I was very proud. We were brave and created chances and scored the second but could not get another. In the second half we played with energy.”
Wembley woes still apparent for Spurs….
- Tottenham have won just one of their past eight matches at Wembley
- Mauricio Pochettino’s side have conceded more goals in four European home games at Wembley this season (six) than they have in 12 Premier League games at White Hart Lane (five)
- Gent became the first Belgian side to eliminate English opposition in major European competition (excluding qualifiers) since Standard Liege knocked out Everton in the 2008-09 Uefa Cup.
- Spurs have been eliminated from eight of their past nine European knockout ties in which they have lost the first leg.
- Since the start of 2013-14, Harry Kane has scored four own goals – twice as many as any other Tottenham player.
Tottenham, who remain without a trophy since 2008, will focus their attention on trying to catch runaway Premier League leaders Chelsea.
Third-placed Spurs host Stoke City at White Hart Lane on Sunday (13:30 GMT).