Tonight Robinson will lead the Dons at the Emirates Stadium against Arsenal in the Carabao Cup and his run so far has been about as unconventional as you can imagine.
It all started with his retirement from football at the age of 16 due to injury and walking away from the game he loved. What followed was a career in the music industry, opening her own children’s room and working as a tour guide at Stamford Bridge.
Robinson’s love for the game eventually brought him back to football and in 2004 he started coaching the Wimbledon Under-9 team.
Over the past 17 years, he rose through the ranks until in February he was named head coach.
“A lot of times it all still feels a bit surreal, but I don’t think that’s a bad thing,” Robinson told Standard Sport. “You never want to get comfortable and get used to it.
“This club means everything to me. My dad had certain values that he instilled in me growing up and it’s just a football club that really keeps giving. This club inspires me.
Wimbledon may inspire Robinson, but his journey should give people the belief that anything is possible.
When he ruptured his quad muscle at the age of 16, Robinson was forced to leave behind a promising youth career at Fulham.
He walked away from acting, working for the music company The Performing Rights Society and there he eventually moved into a management role.
But deep down, Robinson’s love for football was still there. He did community coaching with Crystal Palace, while managing his work team.
A chance encounter with Tony Wilson, whom Robinson played with at Fulham, further fanned the fires when he revealed Wimbledon needed help coaching their youngsters.
Ultimately, Robinson took the leap and quit his job so he could start a business with his wife and trainer in his spare time.
“I really packed it all in, because my passion was coaching,” he says. “We had just had our two children, so we created a place for children. It was a bit like soft play meets Nero coffee.
“It was a huge risk. We borrowed a substantial sum of money – six figures – to open the business. Most indie businesses go broke within five years, but I’ve always been that person if you want to try something, go for it.
The bet is successful. The venue, It’s a Kid’s Thing, was an award-winning hit, and Robinson’s coaching was improving, not least because of his creative way of improving his public speaking.
“I actually went on a guided tour twice a week at Chelsea,” he says. “It was really under pressure because the tour guides were ridiculously good.
“One was an Elvis impersonator, one was a part-time actor, one was a radio DJ and I was like, where do I fit in there?”
Robinson excelled with the Dons’ academy, taking them to memorable runs in the FA Youth Cup, and eventually the top job came his way earlier this year as the club battled to stay in League One.
From day one, he wanted to make players understand that this was a new era. Fans came to paint the training ground blue and yellow, while its values (communication, relentless, ruthless and ownership) were displayed on signs near the pitches.
The grounds themselves have also been changed, with grids laid out as part of his plans to turn Wimbledon into a top team.
And then there was, as a nod to Robinson’s past, the introduction of music.
“It plays from the morning when the staff come in at eight and it stays on all day,” says Robinson, who asked everyone to choose three songs they liked.
“It brings your surroundings to life. But also, it’s about making players and staff aware that everyone is different. If you come to visit the training ground, one minute you’re listening to rap and the next minute it’s Frank Sinatra.
Culture is a big thing for Robinson and he has spent time with England rugby head coach Eddie Jones to broaden his horizons.
Robinson doesn’t impose fines – “if I make someone do something, they’re not doing it for the right reasons” – and instead hammers home the values he believes in.
“All I’ve tried to get the guys to understand is that if you think the way you act on the training pitch doesn’t impact your performance on the pitch, then you have dead wrong. It erodes trust,” he says.
“Little things like when we have an analysis meeting and some people don’t put their chairs away.
“You may not think it has an effect on your teammates but, I’m sorry, your brain doesn’t work like that.
“He could be your best friend, but there’s something in his brain that tells him he can’t really trust you. He can’t rely on you. This translates to the terrain.
Robinson is clearly right as the results on the pitch have transformed under him.
He kept Dons in place last year, despite taking over when the team went 11 games without a win, and now they are seventh in Ligue 1.
He’s revamped the coaching staff, seeking marginal gains by appointing a restart and replacement coach, and Plow Lane fans love the attacking style of play. “On the ball it’s possession based, but we want to play fast and attack and exciting,” says Robinson.
“Off the ball we have to be really aggressive and press high, so hopefully it still feels like a Wimbledon side to the fans – even if the style of play is different.”
Unsurprisingly, Robinson has bled academy players and in three years he thinks the team could be 60-70% homegrown.
Beyond that, Robinson is dreaming big, even bigger than tonight’s game at Arsenal, and he’s confident the fan-owned Dons could play in the Championship.
“100%, definitely,” he says. “There is nothing more powerful than a group of people on the same path, with the same vision.”
Who knows? When it comes to Robinson, anything seems possible.