Wes Brown has experienced at first hand just how cruel football can be.

Brown has been earning rave reviews at the heart of Manchester United's defence in recent weeks and has been tipped for a place in Sven-Goran Eriksson's first England squad on Friday.

Sir Alex Ferguson even lavished praise on him in his programme notes and hailed the 21-year-old's maturity.

But it all went wrong for Brown in the 87th minute as he turned substitute Vicente's cross into his own net to give Valencia a share of the points and deny United a place in the quarter-finals.

That was tough on Brown who had had another solid game alongside Jaap Stam.

The goal, though, was the least Valencia deserved after they bossed the entire second half.

A measure of Valencia's superiority was that they won five corners, while United did not manage even one.

It had all looked so different when Andy Cole fired United ahead in the 12th minute with his 13th goal of the season.

United had survived an early scare when Kily Gonzalez shot just over the bar from a dangerous position in the box.

But then Cole, who had been subdued in the Mestalla, made his mark at Old Trafford to put United in control.

Ruben Baraja gave the ball away and the striker played a one-two with Ryan Giggs on the left before dispatching the return past Santiago Canizares.

That proved to be Giggs' last meaningful contribution and six minutes later there was the all-too-familiar sight of the Welshman coming off injured, presumably with another hamstring problem, to be replaced by Nicky Butt.

The goal forced Valencia, who had won just one of their previous nine visits to England, to be even more adventurous and Pablo Aimar could have levelled.

The inspirational Gaizka Mendieta played the Argentine international clean through only for the £13.7million striker to drag his shot wide.

So far David Beckham had yet to live up to his pre-match billing from Ferguson and the United midfielder has having another quiet game.

Butt was making more of an impression and the Reds substitute drove a shot into the arms of Canizares.

Butt was then booked for a foul on Mendieta and the caution means he will miss the match against Panathinaikos in two weeks' time.

Valencia continued to look dangerous and Fabien Barthez parried a Gonzalez shot to preserve United's slender lead.

The left-back Amedeo Carboni then made a great burst down the left and played an inviting ball across the United goal, but no Valencia player could apply the killer touch.

The Spanish side were knocking the ball about with a swagger not associated with visiting teams.

But despite enjoying the majority of the possession, they could not find a way through United's rearguard, which was once again being finely marshalled by Brown and Stam.

Mendieta was outstanding in the heart of the Valencia side and he was showing Beckham just how to boss a midfield.

Beckham really was having a night to forget in front of watching England coach Eriksson and his poor display was summed up when he was booked for a foul on Carboni.

Beckham was involved in a flare-up with Baraja when the Valencia midfielder felt he had overreacted to a challenge and pushed him in the back to earn a yellow card from referee Hellmut Krug.

The England international continued to come in for some rough treatment and Carboni was cautioned for a late challenge on the midfielder.

Valencia made one late push and Paul Scholes cleared Baraja's header off the line from Vicente's corner.

United did not heed that warning and three minutes from time, Vicente sent over a dangerous left wing cross which Brown knocked into his own net.

It was Valencia's first goal against United in 357 minutes of Champions League football and means the Reds need at least two points from their remaining two Group A games against Panathinaikos away and Sturm Graz at home to ensure a place in the quarter-finals for the fifth successive year.

Teams:

Man Utd: Barthez, Gary Neville, Brown, Stam, Silvestre, Beckham, Keane, Scholes, Giggs (Butt 18), Cole,Sheringham (Solskjaer 63).

Subs Not Used: Rachubka, Irwin, Phil Neville, Yorke, Chadwick.

Booked: Butt, Beckham.

Goals: Cole 12.

Valencia: Canizares, Pellegrino, Baraja, Aurelio, Carboni, Angulo (Sanchez 65), Mendieta, Kily Gonzalez (Vicente 76), Angloma, Carew, Aimar (Albelda 89).

Subs Not Used: Palop, Deschamps, Djukic, Alonso.

Booked: Baraja, Carboni, Mendieta.

Goals: Brown 88 og.

Att: 66,715

Ref: Hellmut Krug (Germany).