He started, and played well, in Fabio Capello's first match as England manager.
Four years on, both men find themselves working in the same country again, but it is a long way from Wembley and even Milan. This evening, 640 miles south-east of Moscow, David Bentley is due to become the first Englishman to play in the Russian League, making his debut for FC Rostov against Dynamo Moscow.
Should Capello, as manager of the Russian national team, catch sight of Rostov's new midfielder he will doubtless recall a period when Bentley, if not necessarily the new David Beckham, was at least the golden one's understudy, regularly coming on as substitute for him in his seven international appearances. Around the same time he scored a goal now enshrined in Tottenham folklore, away to Arsenal and volleyed in from some 40 yards out during the thrilling 4-4 draw that was Harry Redknapp's second match as manager.
''That's what you play football for, what you dream of doing when you're a kid,'' Bentley told The Independent on Sunday shortly afterwards. But that particular dream turned sour, and so on Thursday afternoon he could be found enjoying the hospitality in the garden of a former Rostov club captain, one of those who have pledged to make him welcome in a strange land.
''It's been really good, a nice 48 hours,'' was Bentley's initial impression. ''The medical was fine, five stars, I've trained and had a good session and I'm looking forward to a good game.''
Even this far from home, the cosmopolitan world of modern football has thrown up a couple of familiar faces: Rostov's goalkeeper is Stipe Pletikosa, once a clubmate at Tottenham, and another recent signing is Florent Sinama-Pongolle, formerly of Liverpool, whom Bentley knew from his days in the North-west at Blackburn.
The weather too has been a pleasant surprise – ''It's boiling'' – and today's forecast is for 29C. By mid-December, when the Russian season takes a winter break, that will have dipped to below freezing, and a decision will be made on whether Bentley's loan period should be extended.
With a reputation for the unconventional, whether volleying in from 40 yards, tipping a bucket of iced water over his manager (a disgruntled Harry Redknapp) or declining to go to a European Championship with England's Under-21s, Bentley is just the type of maverick who could decide he loves the place.
But why Russia? ''There were offers [in England] but I thought this was more attractive, a real challenge to be the first Englishman to play here. I thought it would be nice to get away to experience a different style and football culture. Going abroad is something I've wanted to try. My agent Rob Segal had contacted Eliot van Til [another agent] to explore the possibilities of trying Russia, and when the offer came it was perfect. ''
From which it could be deduced that Andre Villas-Boas was no greater a fan than Redknapp had become of Tottenham's record signing. ''It happens a lot of times,'' Bentley said. ''Look at Andy Carroll's situation.
"You go somewhere, but don't fit in. They buy someone, make a mistake and you're left holding the buck for the mistake. I had a difficult time at Tottenham but hopefully some good can come from it and I can crack on from here."
It was another of those boyhood dreams spoilt, for Bentley was a lifelong Spurs fan, one who had nevertheless been through Arsenal's youth system, understandably found it hard to break into the Invincibles team of 2003-04, toughened up on loan at Norwich and thoroughly enjoyed his time at Blackburn before returning to north London in what seemed the perfect move.
''I played for England at Blackburn, then when I came to Tottenham I stopped playing, which was frustrating. I could have got more money elsewhere but for footballing reasons I preferred to join [Juande] Ramos. All my friends were Tottenham fans but I was a peg in a round hole, I just felt foreign in my own backyard. There wasn't a lot of honesty and communication. I think some managers get a bit frightened of talking to players and saying why you've been left out.''
He is adamant about wanting to look forward now rather than dwell on the past: ''I've been training every day for six months without playing a block of games. That's what I need. Hopefully I can kick-start my career here and look back on it as just one of those things you go through.''
Where is Rostov?
FC Rostov are based in Rostov-on-Don, a port city in south-east Russia. The club were formed in 1930 and were promoted into the Russian Top League in 1991. Their best place was sixth in 1998, but they tend to finish between 11th and 14th. Their stadium capacity is 15,842.