The 43-year-old has had some of the biggest names in world football on his physio bench during stints with Tottenham Hotspur (1997-98), Chelsea (1998-2001), Barnsley (2001-02) and Manchester City (2002-2007).
While some of us were discussing what happened at the office party on Friday with John from accounts or Sarah from marketing, Webb was rubbing shoulders - perhaps literally - with the likes of John Terry, Dennis Wise, Robbie Fowler, David Seaman, Peter Schmeichel or Nicolas Anelka.
It was not nearly as lucrative - he now plys his profession at Consultancy House Clinic - or as glamorous as you might think, he said.
But it was a dream job for a while and, professionally, it opened a lot of doors.
"It got me a job down here for one," he said.
"It was nowhere near as glamorous as you'd think. You were doing 60 to 80 hours a week and you're out training on Christmas day - not at home.
"So it wasn't a family-oriented sort of sport. It was hard work and you don't get paid the money people think you'd get."
When Webb realised his family saw him on TV almost as often as they did at home, he decided it was time to make a change.
Born and bred in England, Webb said the decision to emigrate with his wife and five sons was ultimately an easy decision to make.
"There was just too much violence and everything else in England. And everyone I met from this part of the world always seemed to have a good altitude to life. So I was like `Right, where are we going to bring the boys up?'. It was a straightforward decision, really."
The family moved to Dunedin last year and feel settled.
After a decade in the football industry, Webb said his passion for the sport had withered a little but he was rediscovering his love of the beautiful game through coaching his sons (aged 5-10).
"Because you're involved so heavily it becomes a way of life. Therefore you lose interest a little bit.
"I worked seven days a week. I worked a normal job and did two other jobs on top. I did a whole load of study as well and then got to a point where I got my break at Spurs."
Webb has heard his share of gossip from his high-profile patients.
All that tittle-tattle is locked in the vault - patient confidentiality and all that.
But he can reveal, aside from their flush bank accounts and sporting prowess, Premier League players are same as anyone else.
"They are just normal Joe Bloggs people. It is just they have a lot of money because they have got talent and get paid for it.
"But take all that away and they are the same as me and you."
