Owen Hargreaves has been left out of Manchester United's 25-man squad for the Champions League knockout stages.

The 29-year-old England midfielder has been sidelined since 21 September 2008 after undergoing surgery to cure a tendinitis problem in both knees.

United boss Sir Alex Ferguson hoped Hargreaves would be available for the Champions League knockout rounds but he has been replaced by Ritchie de Laet.

The move casts doubt on Hargreaves' hopes of playing at the 2010 World Cup.

Plagued by a tendinitis problem since before his £18m move to United from Bayern Munich in July 2007, Hargreaves has made only 25 starts for the Old Trafford club.

He finally accepted the need for surgery last season and was closely monitored by renowned Colorado-based knee specialist Dr Richard Steadman until his return to United's Carrington training base in September.

At that point, Ferguson was hopeful Hargreaves would feature in the final two matches of the Champions League group phase.

Instead, potential comeback dates kept getting pushed back, with the Ferguson citing the Calgary-born player's lack of confidence for a slower than expected recovery.

Ferguson did, however, suggest last week that Hargreaves - whose contract expires in June - would be among his European options for the rest of the season.

"Yes, Owen will probably be in my Champions League squad," said the Scot. "It will be finalised in the next 10 days and unless something untoward happens I would imagine we will be picking him."

But Hargreaves has seen his place is taken by De Laet, a 21-year-old full back who has made only four starts for United.

Striker Mame Biram Diouf is also in the squad but Danny Welbeck has been removed after joining Preston on loan until the end of the season.

Ferguson's latest fitness bulletin about the Hargreaves confirmed he was alternating his training with the reserve and first-team squads, working for two days and then resting for one.

But still there has been no return to match action and the latest news - which rules him out of February's knock-out round clash with AC Milan - will do little to allay fears over Hargreaves' career.

England manager Fabio Capello said in December that Hargreaves could still be included in his squad for the 2010 World Cup - but that now appears a remote possibility.

Hargreaves was named England's player of the tournament at the 2006 World Cup in Germany.

It really is a shame since he's not a philandering douchebag like John Terry