Sven-Goran Eriksson named a star-studded starting line-up to play Australia, as David Beckham captained the likes of Michael Owen, Frank Lampard and Paul Scholes at Upton Park.
But after going 2-0 down in the friendly, the Swede opted to change his entire team at the break introducing both Jermaine Jenas and none other than Wayne Rooney as a raft of players made their debuts.
Jenas, Rooney and Francis Jeffers combined for the latter to halve the deficit but Brett Emerton's late goal gave the Aussies a 3-1 win.
Rooney became the youngest England player ever that night and would go on to break the goalscoring record but for Jenas, his own international career never quite reached the heights he would've hoped for after that night.
"That first night at Upton Park was probably the greatest moment of my England career," said the former Nottingham Forest, Newcastle and Tottenham Hotspur man.
"Making your debut in a senior international is what any kid dreams about and when it happened it for me against Australia, it was all a bit of a blur, to be honest.
"A lot of the attention on the night focused on Wayne Rooney, who became the youngest player to play a senior international, but I felt like I had done okay in the game after coming on at half time.
"I got man-of-the-match on the day and still have the champagne in the house. It was an occasion I'll never forget and when you are an England player, it changes the way people look at you.
"I remember putting in a cross that Francis Jeffers finished off in that game and it was a fantastic night, even though we ended up losing the game.
"There's nothing like pulling on that England shirt. Your family are looking on, you have your name added to the list of great players who have played for the national team and you start to think about playing in major championships, winning tournaments and achieving great things at international level."
Jenas went on to make another 20 appearances for his country but struggled force his way into the starting line-up and was eventually removed from the equation by Fabio Capello.
Much to Jenas' surprise, the Italian gave Jenas his final cap a year before the 2010 World Cup as the midfielder began to struggle for form and fitness in the second half of his career.
"Up to that point, people say you are a potential international, a star in the making, but when you have that first England cap, it is one of the big targets ticked off in many ways and then you start aiming for more," he continued.
"Yet when I look back at my England career now, I have plenty of regrets.
"Don't get me wrong, I'm happy to have got 21 caps for my country and it is a fine achievement, especially when you consider I was around in the Frank Lampard and Steven Gerrard era.
"It would have been tough to get into the England midfield with players like Michael Carrick, Scott Parker and Owen Hargreaves also competing for a place, but we all had to try and get picked ahead of Lampard or Gerrard and that was never going to be easy."
"I went to the World Cup in 2006, but I was never fully fit at that tournament and the frustration from my perspective was that nothing I could do would change the way the team was selected.
"The midfield was pretty much set with Lampard and Gerrard and that was disheartening for players who were not first picks and getting your head around the reality that you probably wouldn't play got a little disheartening when you met up with England squads.
"Then I felt that I was going to get a run in the side when Fabio Capello took over as manager, as I got the impression that he really like me.
"I played in Capello's first game against Switzerland, scored the first goal in that game and he was delighted with everything I did.
"By the time the next game came around, I had just won the League Cup with Spurs and the manager at the time, Juande Ramos, told me that I should really be pushing to secure a place in the England side.
"I had a sore ankle heading into the next international break, but my club manager was keen to let me do all I could to push my England claims.
"But then suddenly I was dropped from the entire squad. I went from starting the previous game and feeling like I had done well to being dropped altogether."
It was a confusing time for the midfielder, who ended up playing his final game for England against Brazil at just 26 years of age, but despite the somewhat brief rollercoaster ride of being an England player the sense of pride that comes with it remained in tact.
"It was a shame because I felt like I had something to offer but it is what it is," admits Jenas.
"Despite my disappointments, I will always be proud to have played for England as many times as I did."
