Middlesbrough FC 1–1 Tottenham Hotspur on 3 November 2007

Middlesbrough right-back Luke Young fired home from 25 yards to deny his former club Tottenham a win in their first league match under Juande Ramos.

The hosts started brightly, with Gary O'Neill going close, but Darren Bent marked a rare start with a fine run and finish from range to put Spurs ahead.

The striker went close to a second from Jermain Defoe's lay-off, but Young drew Middlesbrough level with a pile driver.

Neither side could net a winner, though Spurs now edge out of the bottom three.

With just three wins between the sides before kick-off, the match got underway as something of an early-season relegation battle.

However, Middlesbrough's preparations had already suffered a blow with Jonathan Woodgate ruled out with a hamstring problem to add to Gareth Southgate's injury concerns.

While Southgate's selection was forced upon him to a large extent, Spurs boss Ramos made a statement by dropping Robbie Keane and Dimitar Berbatov to the bench, with Bent and Defoe preferred up front.

That will do little to quieten rumours about Berbatov's future, and it was perhaps telling that all of sporting director Damien Comolli's summer signings, except the injured Gareth Bale, started.

However, a bright start from the hosts suggested the Spaniard's brave selection would backfire.

Just three minutes were on the clock when O'Neill made the most of an error by Young-Pyo Lee to break free on the right, but the midfielder's slide-rule pass just eluded Stewart Downing on the far post.

With Lee Cattermole and Fabio Rochemback shutting down the midfield, Spurs' new centre pairing of Jermaine Jenas and debutant Kevin-Prince Boateng struggled early.

Brazilian Rochemback went close when he fired wide from 25 yards, while Jeremie Aliadiere's fine run across the area brought a smart block from Michael Dawson.

As the game progressed, though, Bent and Defoe began to show signs of a good understanding and, after the former had gone close from Defoe's dinked past, it was Bent who broke the deadlock.

The £16.5m man latched onto Steed Malbranque's block tackle, drifted inside and punished Chris Riggott's hesitation by firing inside the near post from 20 yards.

It was a goal that had hardly looked like coming from the visitors, but they nearly made it two before the break when Defoe broke on the left of the box and crossed, only for Bent's flick to drift past the far post.

Boro, though, emerged from the break with renewed vigour and Paul Robinson did well to palm Aliadiere's header wide.

However, the equaliser was not long in coming and Young deservedly drew the hosts level with a screamer from 25 yards into the top corner.

It brought a sustained spell of pressure from the hosts, and Tottenham responded by replacing Bent and Defoe with Berbatov and Keane.

A fiery few minutes followed, with Berbatov and Keane linking well without reward and Aliadiere claiming a penalty when his cross hit Dawson's hand.

But with both sides keen not to concede a second after poor starts to the season, neither Robinson nor Mark Schwarzer had a save to make as the game petered out.

The result left Spurs without a league win in nine matches but was enough to take them out of the bottom three, a place and a point behind Boro in 16th.

Middlesbrough boss Gareth Southgate:

"We know what we need to do in games but it's not happening - we keep conceding the first goal and that never makes things easy. But we scored a fantastic goal to draw level and that was deserved after a nice spell of possession. A draw was probably fair.

"The injuries we have at the moment are difficult and it's staggering the number of times we've had to change the team. But those are the circumstances and we have to deal with it."