Tottenham 1 Southend 0
Jermain Defoe sent Tottenham into the semi-finals of the Carling Cup but the Premiership side were pushed all the way by Southend at White Hart Lane.
Defoe slid in with five minutes left in extra-time as the visitors sensed another famous upset.
It was harsh on Efetobore Sodje, who was magnificent at centre-back, and goalkeeper Darryl Flahavan, who denied Spurs with a string of saves until Defoe struck.
Spurs clearly took their opposition seriously. Boss Martin Jol showed the visitors respect by selecting a strong side, although he did rest skipper Ledley King.
The bottom side in the Championship had Kevin Maher and Mark Gower, former Tottenham players, in their starting XI and Gower offered a threat on the left in the early exchanges.
Gower's progress at White Hart Lane was hampered with the likes of David Ginola in the side and, with perhaps a point to prove, he looked determined to make an impression.
He whipped in an early cross, had a near-post effort saved by Paul Robinson and late in the first half curved a long-range effort wide of the upright as the underdogs started with energy, as they did in the last round when they defeated Manchester United.
Shrimpers striker Lee Bradbury made his presence felt with his aerial challenges with Michael Dawson, returning from suspension, and the visitors enjoyed their share of possession.
As is the way playing a Premiership side, though, the more established team were a threat with their pace.
Benoit Assou-Ekotto had Spurs' first effort on goal, curling his free-kick around the wall but seeing the effort saved after Steed Malbranque had been tripped by Alan McCormack.
Malbranque had an effort from a similar position, 25 yards out, in the 13th minute but Flahavan saved again.
Spurs were inches away from breaking the deadlock midway through the first half from a move sparked by Danny Murphy playing in Defoe on the left.
The England striker found Mido and his volley smacked against the underside of the bar and away to safety.
Murphy also glanced a header wide while Flahavan, another hero from the United win, was at full stretch when Defoe leapt to meet Assou-Ekotto's cross from the left.
The visitors had been forced into a change in the 25th minute when veteran defender Spencer Prior, who had already taken a knock on his nose, looked to have picked up a groin injury and was replaced by Peter Clarke.
However, they remained a threat going forward and their busy midfielder McCormack was chasing everything in the middle of the park - it eventually earned him a yellow card on the half-hour mark.
They also had sight of goal on the stroke of half-time when Jamal Campbell-Ryce and Freddy Eastwood had efforts blocked on the edge of the area.
Predictably they had to withstand pressure after the break. Flahavan was forced into another save, four minutes into the second period, when Malbranque curled an effort from the edge of the area.
Defoe then came even closer when Sodje, an imposing figure throughout, misjudged a ball over the top but the England striker lobbed wide.
Edgar Davids was brought on for Teemu Tainio in the 52nd minute, and the Dutchman immediately conceded a foul on McCormack, starting a scrappy spell where both sides struggled for fluency.
Murphy, however, forced Flahavan into a save and Malbranque went wide again.
At the other end, Sodje was close with a header from a corner, with Eastwood almost getting on the end of the effort.
Jol then answered the home fans' calls for Dimitar Berbatov to be introduced, and Murphy was taken off.
However, the Bulgaria striker could not break the deadlock as the match headed to extra-time, although there was time for Flahavan to tip over Mido's header in spectacular fashion, while Lewis Hunt survived a handball appeal in the area.
Berbatov, Dawson and Maher came close with extra-time efforts but it was Defoe who grabbed the winner.
In the 115th minute, Malbranque played the ball out to the left and Mido crossed invitingly for Defoe to slide in.
Eastwood could not direct a header when he was under the Spurs bar, and the hosts held on to book their place in Saturday's draw.
Defoe slid in with five minutes left in extra-time as the visitors sensed another famous upset.
It was harsh on Efetobore Sodje, who was magnificent at centre-back, and goalkeeper Darryl Flahavan, who denied Spurs with a string of saves until Defoe struck.
Spurs clearly took their opposition seriously. Boss Martin Jol showed the visitors respect by selecting a strong side, although he did rest skipper Ledley King.
The bottom side in the Championship had Kevin Maher and Mark Gower, former Tottenham players, in their starting XI and Gower offered a threat on the left in the early exchanges.
Gower's progress at White Hart Lane was hampered with the likes of David Ginola in the side and, with perhaps a point to prove, he looked determined to make an impression.
He whipped in an early cross, had a near-post effort saved by Paul Robinson and late in the first half curved a long-range effort wide of the upright as the underdogs started with energy, as they did in the last round when they defeated Manchester United.
Shrimpers striker Lee Bradbury made his presence felt with his aerial challenges with Michael Dawson, returning from suspension, and the visitors enjoyed their share of possession.
As is the way playing a Premiership side, though, the more established team were a threat with their pace.
Benoit Assou-Ekotto had Spurs' first effort on goal, curling his free-kick around the wall but seeing the effort saved after Steed Malbranque had been tripped by Alan McCormack.
Malbranque had an effort from a similar position, 25 yards out, in the 13th minute but Flahavan saved again.
Spurs were inches away from breaking the deadlock midway through the first half from a move sparked by Danny Murphy playing in Defoe on the left.
The England striker found Mido and his volley smacked against the underside of the bar and away to safety.
Murphy also glanced a header wide while Flahavan, another hero from the United win, was at full stretch when Defoe leapt to meet Assou-Ekotto's cross from the left.
The visitors had been forced into a change in the 25th minute when veteran defender Spencer Prior, who had already taken a knock on his nose, looked to have picked up a groin injury and was replaced by Peter Clarke.
However, they remained a threat going forward and their busy midfielder McCormack was chasing everything in the middle of the park - it eventually earned him a yellow card on the half-hour mark.
They also had sight of goal on the stroke of half-time when Jamal Campbell-Ryce and Freddy Eastwood had efforts blocked on the edge of the area.
Predictably they had to withstand pressure after the break. Flahavan was forced into another save, four minutes into the second period, when Malbranque curled an effort from the edge of the area.
Defoe then came even closer when Sodje, an imposing figure throughout, misjudged a ball over the top but the England striker lobbed wide.
Edgar Davids was brought on for Teemu Tainio in the 52nd minute, and the Dutchman immediately conceded a foul on McCormack, starting a scrappy spell where both sides struggled for fluency.
Murphy, however, forced Flahavan into a save and Malbranque went wide again.
At the other end, Sodje was close with a header from a corner, with Eastwood almost getting on the end of the effort.
Jol then answered the home fans' calls for Dimitar Berbatov to be introduced, and Murphy was taken off.
However, the Bulgaria striker could not break the deadlock as the match headed to extra-time, although there was time for Flahavan to tip over Mido's header in spectacular fashion, while Lewis Hunt survived a handball appeal in the area.
Berbatov, Dawson and Maher came close with extra-time efforts but it was Defoe who grabbed the winner.
In the 115th minute, Malbranque played the ball out to the left and Mido crossed invitingly for Defoe to slide in.
Eastwood could not direct a header when he was under the Spurs bar, and the hosts held on to book their place in Saturday's draw.
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