Wolves missed three penalties to hand Tottenham a 3-2 shoot-out victory following a 2-2 draw in Wednesday's EFL Cup third-round clash.
Tanguy Ndombele and Harry Kane fired Tottenham into a two-goal lead inside 23 minutes but Leander Dendoncker responded for Bruno Lage's men before the interval.
Daniel Podence levelled things up 13 minutes after the break following a mistake from Ndombele, but penalties were required at Molineux as neither side could find a late winner.
Pierluigi Gollini managed to save from Dendoncker and with both Conor Coady and Ruben Neves faltering, Spurs marched into the fourth round despite Pierre-Emile Hjobjerg missing.
Ndombele opened the scoring with 14 minutes gone, getting the better of Coady before drifting inside Willy Boly and slotting through John Ruddy's legs.
The visitors doubled their advantage nine minutes later, with Dele Alli carving open the Wolves defence before Kane drilled into the bottom-left corner.
However, Dendoncker halved Spurs' lead as he climbed the highest from Rayan Ait Nouri's outswinging corner to head into the top-right corner.
Alli and Kane attempted to link-up once more after half-time, but Ruddy was on hand to deny the former before Ndombele was at fault for Wolves' equaliser.
The France midfielder was caught in possession by Hwang Hee-chan, with Dendoncker subsequently finding Podence, who curled into the bottom-right corner to level.
Kane's header almost restored Spurs' lead but Ruddy's reflex save kept the scores level before Neves' deflected strike clipped the crossbar as the tie headed towards penalties.
Neves blasted over the fifth spot-kick after the first four had all converted before Dendoncker saw his low effort saved by the Spurs goalkeeper diving to his right.
Hojbjerg could have won it for the visitors but Ruddy denied the Denmark midfielder. However, that did not matter as Coady smashed into the crossbar to hand the away side their place in the fourth round.
Rumour Has It: Tuchel pushes for Tottenham's Kane as Bayern Munich's top priority
New Bayern Munich boss Thomas Tuchel has reportedly communicated to the board that Tottenham striker Harry Kane is his top priority in the upcoming transfer window.
Kane, 29, is just five goals away from overtaking Wayne Rooney for second on the Premier League's all-time leading scorers list, after recently surpassing Rooney as England's all-time top scorer and Jimmy Greaves as Tottenham's record holder.
With his personal legacy in England already secured, the logical next move is somewhere the striker can secure some team silverware, and that is an area Bayern can deliver.
While Tottenham will be desperate to convince their star to stay put, any indication that he will not sign a new contract will likely force the club to cash-in on their top talent.
TOP STORY – TUCHEL HOPING TO MAKE KANE BAYERN'S NEW CENTREPIECE
According to Football Insider, Tuchel "is a huge fan of Kane from his time in the Premier League managing Chelsea", and he has communicated to the Bayern board that he should be the main focus going forward.
Despite Kane approaching the final 12 months of his deal, Tottenham are still expected to demand a fee in the £100million (Є113.8m) range to part ways with their club icon, but it remains exceedingly unlikely that they will allow his contract to run out.
However, the report adds Kane would potentially be open to an extension if Spurs can secure former Bayern boss Julian Nagelsmann as Antonio Conte's replacement.
ROUND-UP
– 90min reports 27-year-old Manchester City midfielder Kalvin Phillips is prepared to leave the club amid concerns his limited playing time will affect his spot in the England team, but Football Insider claims Phillips is prepared to stick it out.
– According to Sport, all 29 MLS clubs have agreed to split the salary of Lionel Messi and would allow him to choose whichever franchise he would prefer.
– Paris Saint-Germain are planning to capitalise on a two-week window at the start of July when 26-year-old Napoli centre-back Kim Min-jae has a temporary release clause of €52.5m, per Foot Mercato.
– Fichajes reports Barcelona will likely be forced to sell 20-year-old winger Ansu Fati in the next transfer window for financial reasons.
Netherlands 3-0 Gibraltar: Ake nets twice as Koeman gets first win of second spell
Ronald Koeman claimed the first win of his second spell in charge of the Netherlands as the Oranje dispatched 10-man Gibraltar 3-0.
Nathan Ake scored twice in a game that saw the Netherlands have 50 attempts without allowing one at the other end, as Koeman's team got up and running in Euro 2024 qualifying following last week's heavy defeat to France.
Ake's second-half double came after Memphis Depay had put the Dutch ahead against the Group B minnows in Rotterdam on Monday.
It marked a 19th straight defeat in Euro qualifying for Gibraltar, who had Liam Walker sent off for a rash challenge on Dutch debutant Mats Wieffer.
In need of a response following their hammering in Paris, the Netherlands had control from the off, and the lead came in the 23rd minute.
Following a patient move, Denzel Dumfries – back from suspension – supplied an inviting cross that Depay glanced in.
Georginio Wijnaldum volleyed just over while Wout Weghorst twice went close – spurning a great chance when he shot wide from eight yards out before Dayle Coleing produced a smart reflex save to deny the Manchester United striker.
The Dutch doubled their lead five minutes after the break, Dumfries helping a deep cross back into the centre for Ake to head home.
Gibraltar were reduced to 10 men less than 60 seconds later. Walker caught Wieffer with a dangerous challenge, leaving referee Morten Krogh with little choice but to brandish a straight red.
Coleing denied Donyell Malen and Cody Gakpo while Roy Chipolina blocked Weghorst on the line, but Ake's deflected strike eight minutes from time added gloss to an easy victory.
Reynolds and McElhenney's Wrexham get their Hollywood meeting with Man Utd
Ryan Reynolds and Rob McElhenney are taking Wrexham to the United States, where the non-league club will face Manchester United.
San Diego's Snapdragon Stadium will host the friendly on July 25.
Wrexham, who this month signed former United goalkeeper Ben Foster, are pushing for promotion from the National League.
They sit three points clear of Notts County, while they also reached the fourth round of the FA Cup, losing to Sheffield United, who have gone on to reach the semi-finals.
The Welsh club were bought by Hollywood A-listers Reynolds and McElhenney in 2020.
"We're looking forward to being able to play in the United States for the first time in the club's history," said Wrexham manager Phil Parkinson.
Wrexham last faced United in an FA Cup tie in 1995. The Red Devils' team will be mainly made up of academy players.
SportsMax is the Caribbean sports channel of choice, committed to providing sporting content of the highest quality to the Caribbean, delivered by a team of highly innovative, passionate and qualified professionals.
(876) 619-7629
digitalmedia@sportsmax.tv
