Harry Redknapp arrived at Tottenham in October 2008 after the sacking of Juande Ramos. Now, on first thought it might seem odd that a club would dismiss so quickly a manager that had delivered them a trophy only a few months ago, but it’s important to point out that Spurs had started the 2008/09 season in the most atrocious of fashions and were seated firmly in the relegation zone by October, which is unquestionably unacceptable for a club of their stature, and so they turned to the other guy who had won domestic silverware last season (Redknapp won the 2008 FA Cup with Portsmouth).
And what better way for Redknapp to get his feet under the table than a nice, cozy affair like the North London Derby?
And what a game this opener would turn out to be, a game for the ages as Redknapp’s Tottenham immediately set the tone for how his term was going to be remembered. In this article we take a look at the first-ever Tottenham starting XI fielded by Harry Redknapp.
Arsenal 4-4 Tottenham | October 29, 2008
Tottenham, set up in a 4-5-1, drew first blood with a strike from former Gunner David Bentley for the ages. Arsenal, however, quickly established their dominance by scoring the next three goals. Spurs pulled one back the second half, but Arsenal restored their two-goal advantage within a minute and would go on to lead by that margin with less than two minutes of regular time remaining when late, late goals from Jermaine Jenas and Aaron Lennon earned Spurs a point.
GK | Heurelho Gomes
Having joined only in the summer, Gomes remained Spurs’ first-choice keeper under Redknapp, making nearly 50 appearances in the 08/09 season. He would go on remain on the club’s book till 2014 before moving on to Watford. He retired in 2021.
DEF | Alan Hutton
Hutton’s first game under Redknapp set the tone for his first full season at Spurs and in general his stint in North London, as he would go on to just 11 times this season across all competitions. He moved to Aston Villa in 2011.
DEF | Vedran Ćorluka
Summer arrival Ćorluka would remain one of Redknapp’s first names on the team sheet for most of his three-and-a-half-year stay at White Hart Lane. This season alone saw him feature 47 times across all competitions.
DEF | Jonathan Woodgate
This was the only season in which Woodgate, having arrived from Middlesbrough after his ill-fated Real Madrid stint, served as one of Spurs’ first-choice defenders, making 44 appearances across all seasons. He would go on to make only four more over the next two years.
DEF | Benoît Assou-Ekotto
Assou-Ekotto spent nine years on Spurs’ books (2006-2015), the longest stay at a club of his entire professional career. In the 08/09 season, he featured for Spurs 36 times across all competitions.
MID | Luka Modrić
What more can we say about this guy? After arriving in the summer from Dinamo Zagreb, Modrić remained one of the first names on the Spurs team sheet for the four seasons he spent at White Hart, establishing himself as one of the best midfielders in the league that earned him a €35m move to Real Madrid, and the rest is history.
MID | Jermaine Jenas
Even though injuries would hamper him soon and bring his career to a premature halt, Jenas was a regular for Redknapp this season, making 39 appearances across all competitions.
MID | Tom Huddlestone
Even though Huddlestone is revered as much as his other contemporaries, he was one of the finest passers of the ball on his day. This season, he featured rather sporadically for Spurs, making 31 appearances deep in the midfield across all competitions.
MID/FWD | David Bentley
Most of us know David Bentley’s “I fell out of love with football” story, which often makes one think how great his career could otherwise have been.
Not that Bentley did not have a career of some renown at all, and his ability was on full display in his particular game as he opened the scoring for Spurs with a wonder-strike.
MID/FWD | Gareth Bale
Another to-be Real Madrid man. It was under Redknapp that Bale truly transitioned from an exciting fullback with a penchant for attack to one of the most lethal forwards in world football.
This season, Bale mostly played as a fullback and wingback, making 30 appearances and providing three assists without any goals.
FWD | Roman Pavlyuchenko
The 6’3″ Russian was quite the operator up front for Spurs, especially when Redknapp deployed him alone in the absence of the Peter Crouch-Jermain Defoe duo. This season, Pavlyuchenko provided 14 goals and 3 assists from 37 appearances across all competitions.
