Theo Walcott spent over a decade at Arsenal, arriving as a teenage prodigy and departing as a club legend with over 100 goals to his name. The former England international - who is the youngest footballer to play for his nation - took to the field alongside some of the Premier League's biggest names, including Arsenal's all-time leading scorer, Thierry Henry.
The winger's journey in North London began in 2006, when he joined from Southampton at just 16 years old. He rubbed shoulders with the likes of Cesc Fàbregas, Robin Van Persie and Alexis Sanchez during his 12-year stint at the Emirates. While Henry's flair and undoubted talent took supporters to their feet, it was Ashley Cole who stood out for Walcott for his sheer dominance in defensive duels.
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Theo Walcott Picks Ashley Cole as One-On-One Master
He is one of the best left-backs in Premier League history
Arsenal's Theo Walcott (L) in action with Chelsea's Ashley Cole (R)
Cole earned the highest praise from his peer, mainly for his work behind closed doors. Speaking to FourFourTwo, Walcott recalled the relentless battles between Cole and Henry during training sessions, revealing how the full-back consistently came out on top. The Frenchman tried to do his best to outfox him with pre-declared moves, but that just wasn't enough. Walcott said:
"[Cole] looked after me at Arsenal, I’ll never forget that, and he’s probably the best left-back in Premier League history.
"We often practised one-on-ones, and it was difficult to get past him. I’d watch him do drills with Thierry Henry after training. Thierry used to say what he was going to do before he did it, but Ashley always came out on top in those battles.”
Cole's Legacy Lives On
A three-time Premier League winner
ashley-cole-chelsea-fa-cup
Ashley Cole's time at Arsenal spanned from 1999 to 2006, during which he won two league titles and three FA Cups. His impressive displays in Gunners red earned him a controversial move to London rivals, Chelsea. It was a £5 million transfer which saw French defender William Gallas join Arsenal to bolster their damaged backline.
At Chelsea, Cole's brilliance reached even greater heights. He added another Premier League title to his name, as well as four more FA Cups, a League Cup, and the coveted Champions League trophy in 2012. His time at Stamford Bridge solidified his status as one of England's greatest ever defenders, with his game oozing in versatility and quality.
For Walcott, who arrived just as Cole was leaving, the defender's mentorship and on-pitch tenacity left a lasting impression. Those training ground showdowns with Henry only cemented his reputation as an immovable force at the back.
After retirement, Cole fell in love with coaching, and enjoyed important roles at Derby County, Everton and, most recently, Birmingham City. However, in September 2024, he announced he was leaving the Midlands side to join up with the FA to form part of the backroom staff for the England national team.
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