Theo Walcott made his final career appearance when Liverpool visited Southampton in May 2023. The then 34 year old contributed an assist in a thrilling 4-4 draw, marking the end of his professional career with relegation.
Despite being a lifelong Reds supporter, Walcott's record against Liverpool was somewhat disappointing. In 27 appearances, he only managed six victories, scoring two goals and providing three assists.
However, two of his most memorable moments for Arsenal came against Liverpool, as he ran the length of the pitch to claim assists at Anfield in the Champions League in April 2008 and again in the Premier League a year later. Walcott spent the majority of his career with the Gunners, joining from Southampton in January 2006 for £12m.
He made 397 appearances over 12 years, netting 108 goals before moving to Everton for £20m in January 2018 and later returning to St. Mary's, initially on loan, in October 2020.
Despite winning the FA Cup twice during his time in North London, it is perhaps surprising that the 35 year old did not achieve more, given the high expectations when Arsenal first signed him from Southampton. Although frequently linked with a move to Liverpool throughout his career, such a transfer never materialised before he joined the Reds' fierce local rivals.
Despite being a boyhood Liverpool fan, Theo Walcott admitted he couldn't turn down the opportunity to join Arsenal in 2006, thanks to the persuasive powers of Arsene Wenger and the chance to play alongside his idol, Thierry Henry.
Reminiscing on Sky Sports' Monday Night Football earlier this season, Walcott disclosed: "Chelsea and Liverpool were options at the time," adding that "Manchester United came in very late, which I was unaware of, but to be honest my mind was already made up as soon as Arsene Wenger got involved. I remember going back to his place with David Dein."
He gushed about his aspirations, stating: "Thierry Henry was a player that I really aspired to learn from and as soon as I learned Arsenal were involved I thought I have to go there and play with him."
Walcott highlighted the allure of playing with a football star reflecting any youngster's dream: "It was my dream to play with someone like that. You ask any kid who you get an opportunity to play with your [dream] star, you're going to do it. It was an easy option for me."
In a curious twist, he shared how he rejoiced Liverpool's previous Champions League victory, saying: "When Liverpool won the Champions League last year, I went mad. I was shouting so loud I think I woke up the entire village where I live!"
Despite ultimately signing for the Gunners, Walcott also held a connection to Chelsea, having been a ball-boy there — a unique chance to be close to Liverpool players like Michael Owen and Robbie Fowler, whom his father admired.
He remembered: "I was playing in a tournament for Swindon when Southampton and Chelsea showed an interest.
"Chelsea invited me to be a ball boy for a match against Liverpool and it was fantastic to meet my heroes Michael Owen and Robbie Fowler."
"I was a Liverpool fan simply because my dad followed them. Unfortunately I wasn't born when the team had their golden era, but I enjoyed watching the likes of Michael Owen, Robbie Fowler and Steve McManaman when I was growing up."