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Having started his career trawling the streets of Croydon looking for footballing talent, the 45-year-old could complete an astonishing journey by coaching Georgia at the 2026 World Cup.
A teenager with dreams of making it as a footballer, Webb was let go by boyhood club Crystal Palace before turning his hand to coaching the club’s under-10s and under-11s.
Palace are now known for developing raw talent and he was probably the first in that line of talent. He was very skilful, very athletic and he was lightning quick and could score goals for fun.
His role included an element of scouting for the club’s youth academy and it was then that Webb’s eye for talent became apparent when he went off the beaten track to bring a player to the club who would go on to became a true great – Wilfried Zaha.
Speaking to talkSPORT.com, Webb explained: “At the time, Palace weren’t really looking at him. He came from an area in Croydon that wasn’t the most fashionable and the leagues and facilities he was playing with weren’t the best.
He was only ten but he had this real desire and aggression about him which is hard to see in young players but he had no fear when he played.
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“He had a six-week trial and he struggled a bit with the coaching from grassroots to academy football and he hadn’t played any games. I remember the coach saying to me ‘we don’t know what to do with him’ and I said ‘we need to see him in a game before we make any decisions’.
“So he put him in against Tottenham’s academy and the coach rang me afterwards and said, ‘yeah, we’re signing him – we won 6-4 and he scored all of them’.”
Webb’s ability to identify and coach young talent caught the eye of Tottenham where he worked between 2003 and 2006 in a similar role, before being appointed as academy director with Millwall.
As well as taking his first foray into European football with some consultancy work with Bayer Leverkusen, Webb believes that it was his time working in some of London’s best youth academies that laid the foundations for what was to come next.
“I spent my first seven or eight years at top academies in England where I really learnt my grounding,” he explained.
He worked closely with Eddie Howe during his Bournemouth days
“If you look at the top coaches now, a lot of them say that working in the academies or working with top-end youth players really helps them to get a grasp of coaching, particularly the teaching and developing side of it.”
With Millwall losing their academy status, Webb joined Southampton in a youth recruitment role, before making his first step into the first team after impressing then-head coach Mauricio Pochettino and Paul Mitchell – the Newcastle sporting director who was working as the Saints’ head of recruitment at the time.
Snapped up by Bournemouth as head of senior recruitment, Webb worked closely with Eddie Howe and helped the Cherries to sign first team stars including Callum Wilson, Dan Gosling, Josh King and Adam Smith before returning to Tottenham as head of elite identification.
Working with the 17-21 age group and then the first team, Webb played a key role in helping Spurs to sign Kieran Trippier, Tony Alderweireld, Jan Vertonghen and Christian Eriksen, but it was the signing of Dele Alli that really stands out.
Now rebuilding his career in Italy with Como, Webb say that he’s hopeful to see the midfielder get back to showing his undoubted qualities.
Asked about Dele’s return with Como, Webb said: “It’s really pleasing because he’s such a nice lad. He deserves it and he’s still got age and time on his side.
Working with the 17-21 age group and then the first team, Webb played a key role in helping Spurs to sign Kieran Trippier, Tony Alderweireld, Jan Vertonghen and Christian Eriksen, but it was the signing of Dele Alli that really stands out.
Now rebuilding his career in Italy with Como, Webb say that he’s hopeful to see the midfielder get back to showing his undoubted qualities.
Asked about Dele’s return with Como, Webb said: “It’s really pleasing because he’s such a nice lad. He deserves it and he’s still got age and time on his side.
He’d come from League One to the Premier League and it was a bit of a jump but because of his application, the way he trained and his sheer will and determination he forced his way in and once he was in and played Premier League games he became a regular starter and that’s testament to him that he had that about him
“He didn’t fear playing for Tottenham after coming from MK Don, he just knew it was where he belonged.
“It’s great to see him back now because he still has a lot to offer.”
Three years with Tottenham passed before joining Swedish side Ostersunds as technical director and then Huddersfield as head of football operations in 2019.
Webb’s first move into management came with York City where he was hospitalised in his first week in charge with pneumonia, before being sacked within two months.
But having built an impressive network of contacts within the game, Webb got the call from France and Bayern Munich legend Willy Sagnol about a surprise opportunity to work as his assistant coach with the Georgian national team.
In their first full qualifying campaign together, Sagnol and Webb led Georgia – including superstar Khvicha Kvaratskhelia – to the Euro 2024 finals – their first-ever major international tournament.
Not just happy to make up the numbers, a victory over Cristiano Ronaldo’s Portugal saw Georgia progress from the group stage and into the last 16 where they were eliminated by Spain despite a spirited display in a 4-1 defeat.
But not happy with that achievement, Webb is aiming even higher next time around.
