Tottenham Hotspur 1 Southend United 0 (After Extra Time): Defoe strikes in extra time to break Southend

The Football League will only have one of its clubs in the semi-finals of its cup competition next month but they were sorely close to having double that total here last night.

After the heroics from Wycombe on Tuesday night, Southend were within five minutes of forcing a penalty shoot-out and seriously entertaining the possibility of claiming a victory almost as prestigious as the one they pulled off in the previous round against Manchester United.

That it was not to be was down to Jermain Defoe, who poked a leg out to meet Mido's cross from six yards out, with a suspicion of offside. In truth, Spurs should have been out of sight long before Defoe's fourth goal in as many games, but thanks to Darryl Flahavan, their goalkeeper, the Shrimpers resisted far longer than anyone would have predicted.

For Freddy Eastwood in the last round, read Flahavan in this. The former was the hero in winning the tie against Manchester United last month and the latter kept his teammates alive in this League Cup quarter-final, frustrating Spurs into looking an increasingly ragged and disorganised outfit. Spurs manager Martin Jol observed: "We lacked creativity, but they made it difficult. Southend looked a good footballing side. It's amazing they are bottom of the Championship."

Several times Flahavan kept out efforts from, among others, Mido, Defoe and Steed Malbranque. Prior to Defoe's match-winning effort, when Flahavan was beaten he had luck on his side, in the equally solid form of the crossbar, all of which forced this game into extra time.

Jol had not taken Steve Tilson's side lightly, nor had he fielded his strongest side, bearing in mind the fact the Essex side's league position and Spurs travel to Newcastle on Saturday.

Out were the injured Aaron Lennon and Hossam Ghaly as well as the suspended central midfielder Didier Zokora, while Jol opted to rest Ledley King, Pascal Chimbonda and his free-scoring striker Dimitar Berbatov.

The plan backfired, however, as he was forced to bring on the Bulgarian late on in normal time. That then forced Mido out on to the left wing, from where the Egyptian, who otherwise endured a fairly fruitless night, crossed for Defoe's vital strike.

For the visitors, coming to White Hart Lane was an altogether different test after beating Manchester United at Roots Hall. Eastwood, so key to their hopes of causing another upset here, looked bright throughout as did Jamal Campbell-Ryce out on the right wing, where his pace troubled Benoit Assou-Ekotto.

Spurs' early attempts were from long-range, with Assou-Ekotto, from a free-kick, and then Malbranque after 13 minutes, testing Flahavan's handling.

Spurs went close to opening the scoring after 23 minutes. Defoe turned provider from the left and Mido's left-foot volley from 12 yards hit the crossbar but ricocheted down and away from danger. Not that Southend were sitting back, and Mark Gower, a former Spurs player, cut inside Stalteri and tested Paul Robinson from 20 yards. However, their best chance fell to Efe Sodje, rather than Eastwood, after 75 minutes, but his header dropped just wide.

The danger refused to go away for Southend when another Stalteri cross was headed just wide by Danny Murphy. Soon after, the hosts went close once more, this time as Defoe brought another fine save, with Flahavan tipping his header around the post.

Yet there was better to come from the goalkeeper when he turned Mido's header, which was going into the top corner, over the crossbar in the 90th minute, forcing extra time. When Defoe did score, Tilson, who acclaimed his side's "fantastic performance", felt that replays confirmed that the England international was offside.

"We matched them for 90 minutes," he said. "I'm just disappointed we didn't take them to penalties and it was tough to see the goal was offside. As for us, we just lacked a goal."

Tottenham Hotspur (4-4-2): Robinson; Stalteri,Dawson, Davenport, Assou-Ekotto; Tainio (Davids, 56), Huddlestone, Murphy (Berbatov, 76), Malbranque; Mido, Defoe. Substitutes not used: Cerny (gk), Lee, Gardner.

Southend United (4-4-2): Flahavan; Hunt, Prior (Clarke, 25), Sodje, Hammell; Campbell-Ryce (Hooper, 113), Maher, McCormack (Francis, 117), Gower; Bradbury, Eastwood. Substitutes not used: Welch (gk), Paynter.

Referee: P Dowd (Staffordshire).