Tottenham had to go into penalties to subdue a stubborn Hull City and advance to the last eight of the Capital One Cup in a highly competitive game late on Wednesday night.
After a miss apiece in the first five kicks, Ahmed Elmohamady was denied by Brad Friedel to decide the tie.
Gylfi Sigurdsson’s first-half 25-yarder had put the home side ahead, before Freidel fumbled into his own net.
Paul McShane nodded home in extra time to give the visitors the lead for the first time, but substitute Harry Kane’s low shot sent the game to spot-kicks.
Andre Villas-Boas’s side have now won nine of their last 11 games, after beating the same opponents three days earlier in the league.
The home crowd responded well to their Portuguese manager’s demands for an improvement on the weekend’s atmosphere at White Hart Lane with raucous support from the first whistle.
Villas-Boas’s players were a little slower to get into their stride, but after Younes Kaboul had planted a header wide, Sigurdsson’s explosive strike repaid their fans.
The Iceland international swivelled to leave Curtis Davies in a heap before sending a fierce shot beyond Eldin Jakupovic and in off the underside of the bar.
Tigers boss Steve Bruce, who talked his way into a Football Association charge with his complaints over the penalty that decided the league meeting between the two sides, was incensed once again when Kyle Walker escaped a booking for a heavy challenge on Stephen Quinn just before half-time.
His frustration seemed to translate into an effective team talk however and substitute Aaron McLean twice shot at goal before his side pulled themselves level seven minutes into the second half.
George Boyd’s clever flick found Liam Rosenior whose low cross was met by a sliding Davies at the far post. The former Aston Villa defender contrived to screw his shot across, rather than into, goal, but Tottenham goalkeeper Friedel’s attempts to keep it out did the opposite.
Davies and McLean threatened for Hull, but Spurs substitute Harry Kane came closest to a winner in normal time, having a goal disallowed for a Jermain Defoe hand-ball before rattling the crossbar deep into injury time.
Instead McShane put his side ahead for the first time after outjumping Vlad Chiriches to meet George Boyd’s corner and the visitors could have made the game safe had Gedo kept his head 12 yards out shortly after.
But Kane got the goal he deserved in a spiritedly display, working himself clear of the attentions of McShane and drilling home a low shot.
Despite the crowd urging them forward, Tottenham could not find a winner in normal play and had to face up to a wretched run of form in penalty shoot-outs – they have not won one since 1994.
Hull’s McLean and Erik Lamela for the hosts were the only players to falter in the first 15 attempts, before Elmohamady planted his shot too close to Friedel.
Despite successive defeats in north London, Hull will take plenty of heart from the quality of their performances going into Saturday’s match against Bruce’s former charges Sunderland.
In the other match, Alvaro Negredo and Edin Dzeko scored in extra time to earn Manchester City a place in the Capital One Cup last eight at the expense of Newcastle.
In a largely lacklustre tie, the hosts created the better openings with Costel Pantilimon saving Shola Ameobi’s shot.
But after Pantilimon again saved expertly to deny Papiss Cisse in extra time, Negredo tucked in Dzeko’s cross.
Dzeko then rounded Tim Krul after a slick move as City secured their ninth successive win over the Magpies.
Joleon Lescott cleared a Hatem Ben Arfa shot off the line as the game came to a finish but City progressed safely to a quarter-final meeting with Championship side Leicester.
The two late goals by the visitors offered flashes of quality after both teams had laboured in front of goal during normal time.
It was a game that was a far cry from City’s 4-0 win over the Magpies in their first game of the season. City – who made 10 changes to the side that lost to Chelsea on Sunday – offered less of a threat than the hosts for most of the match, and relied on two fine saves by Pantilimon to keep them in the tie.
The Romanian had been expected to feature, having played in the last round, but his performance will give City boss Manuel Pellegrini something to ponder after a Joe Hart error gifted Chelsea victory at Stamford Bridge. It was City’s first clean sheet in seven games.
Cisse twice wasted good chances for Newcastle in the first half as he lobbed the ball wide after the industrious Ameobi flicked on Krul’s kick, and miscued a shot from close-range.
It continues a poor run in front of goal for the Senegalese forward, who has managed one goal in his past 15 games.
The visitors lost Stevan Jovetic to what looked like a calf injury early on and although Negredo joined Dzeko in attack, City were missing the punch provided by the rested Yaya Toure and Sergio Aguero.
Right-back Micah Richards, who captained the side, headed over from a promising position early in the second half before City almost took the lead against the run of play – Krul misjudging a through ball down the right but Milner failing to find the target with the goal gaping.
Once David Silva was introduced after the hour, City began to offer a greater threat, with Negredo twice going close.
Nevertheless, Newcastle should have gone ahead in the first period of extra time, but again Cisse was wasteful. The Newcastle forward was found expertly by substitute Ben Arfa but Pantilimon clawed his shot away.
The Magpies having spurned that chance, Spanish forward Negredo finally took advantage, leaving Mapou Yanga-Mbiwa flat-footed for the first before Milner exchanged passes with Silva to set up Dzeko, who sealed it 15 minutes left.