When Tashan Oakley-Boothe first stepped up to train with Tottenham Hotspur’s first team squad as a promising teenager, he could hardly have imagined that years later he would be reunited with one of the senior players who made such an impression on him at the time – not at the gleaming facilities in North London, but at KDM Group East End Park in Scotland.
Tashan’s time at Tottenham was formative in more ways than one. Joining the academy system in July 2017, he quickly found himself rubbing shoulders with some of the biggest names in football. Within three weeks of his arrival, he was making his senior debut as a half-time substitute against PSG in a pre-season friendly in Orlando – a remarkable introduction to top-level football for any teenager. The midfielder became Tottenham’s first millennial to play a competitive game for the club when he came on against Barnsley in the Carabao Cup in September 2017.
Now 25 years old, the midfielder’s journey from Spurs academy graduate to Dunfermline Athletic player is one marked by perseverance and professional growth, but it was given an unexpected twist when Victor Wanyama arrived at the club on a short-term deal in March this year.
Tashan shared his time at Spurs not just with Victor but with big names like Vertonghen, Sissoko, Dembele and Son. He recalls. “It was an incredible environment to learn in.” But it was his relationship with Victor Wanyama that would prove most memorable, albeit for reasons. For nearly two years, the young Tashan found himself training alongside Wanyama, learning from a player who had already established himself as one of the Premier League’s most reliable midfielders. However, the education came with some painful lessons:-
“I had to look out for him when I was younger. He just used to step on my toes,” Tashan laughs. “When I went up to the first team, I didn’t want to go anywhere near him. I warned everybody here before he came – I said watch your toes in training.” The warning proved to be more nostalgic than necessary. “He’s not like that anymore.”
Despite the bruised toes, Tashan recognised even then the value of training alongside someone of Wanyama’s calibre. The Kenyan international went on to earn 64 caps and notched up approaching 500 senior appearances across clubs like Celtic, Southampton, and Tottenham. He represented everything a young player could aspire to achieve.
“You can’t pay for experience,” Tashan says. “It’s people that have been there and done that. Especially for younger players, I think it’s important to learn from the experienced ones because they’ve been there and done that. They’ve worn the shirt.”
When Wanyama signed his short-term deal with Dunfermline in March, joining the club for the final seven matches of the season, it created a unique opportunity for both players. For Tashan, who had joined the Pars the previous month, it was a chance to play alongside his former mentor as equals.
“Of course he remembered me. I was with him quite a lot when I was young. For almost two years. So yeah, we were quite close, to be fair. We only played one game together, to be fair at Morton. I quite enjoyed it. I knew how he played, so it was easy to bounce off him.”
While Wanyama’s time at Dunfermline was brief – just four appearances – his impact, not just Tashan Oakley-Boothe but on all the squad demonstrates the value that experienced professionals can bring to any dressing room, regardless of the level. For Tashan, the re-union served as a reminder of how far he had come since those early days at Tottenham’s training ground, dodging Wanyama’s feet and absorbing lessons that would serve him throughout his career. Their time together at Dunfermline stands as a unique chapter – a reminder that football connections often transcend the boundaries of individual clubs and competitions.
The story has taken on an even more positive dimension with the announcement on 13th June that Tashan had signed a one-year extension to his contract, meaning he will be at KDM Group East End Park for the upcoming William Hill Championship campaign. With a full pre-season under Neil Lennon ahead of him, Tashan is hoping to play a vital role for Dunfermline in the 2025-26 season.