The experiences that brought him to a World Cup semi-final include being snubbed by a current England team-mate, nutmegging Luka Modric and Euro 2016 heartbreak against Iceland.
Alli, who scored the second goal in England’s 2-0 win quarter-final win over Sweden on Saturday, says he does not get nervous, but agreed that tomorrow’s clash against Croatia is his grandest stage yet.
An apt time, then, to reflect on his road from the MK Dons youth system to the Luzhniki Stadium.
Asked to name his toughest experience in the lower leagues, the 22-year-old Tottenham midfielder barely missed a beat before answering “Bradford away”.
It was February 2015 and Alli scored in a 2-1 defeat at Valley Parade, but neither that, nor the appearance of England No 1 Jordan Pickford in goal for the Bantams, is lodged in his mind.
“It was a night game, the pitch was horrible,” he said. “It was a horrible game. They were very aggressive and it wasn’t a nice day. Every time I got the ball people would be kicking, swearing.
“There are a lot of different paths you can take to getting to the England senior team.”
Rewind six months from that match and Alli was announcing himself as one to watch with a confident performance in a shock League Cup win for MK Dons over Manchester United under their then new manager Louis van Gaal.
The League One side recorded a stunning 4-0 win, but Alli was still a wide-eyed teenager, who sought out United striker Danny Welbeck for a souvenir shirt.
The suggestion was politely rebuffed – a fact the pair are now able to laugh about as England colleagues in Russia.
“Me and Danny Welbeck have a joke about it because I asked him for his shirt,” Alli laughed.
“We speak about it now. He wouldn’t give it to me. I think he wanted to keep that shirt, but he was polite about it. He was really nice. I wasn’t going to give him mine – I just wanted his.”
Come tomorrow it could be Croatia star Modric with whom Alli will want to swap jerseys.
The pair will both be key in the battle for midfield supremacy and have previous with each other – including Tottenham’s Champions League win over Real Madrid last November.
Alli had yet to play a competitive game for Spurs when he nutmegged Modric in a 2015 pre-season friendly – earning a cheerful rebuke from his more established opponent.
“I remember it... he said something,” Alli recalled with a smile.
“I always enjoy a good nutmeg. I didn’t shout ‘megs’. I have never done that, even in training. Some people when they nutmeg (someone), they call it, but it’s never been something I’ve done.”
Asked if a repeat performance was on the cards, he said: “Nutmeg him? Hopefully. But I’m not going to focus on that.”
Not all of Alli’s memorable moments are good ones, with the nadir being England’s Euro 2016 exit to Iceland.
Thinking back to a time when a World Cup final must have seemed an implausible prospect, Alli said: “Straight after that game you want the floor to eat you up.
“You want to hide and not come out of your room. You want to forget about it and lock yourself away.
“When Gareth (Soythgate, England’s manager) came in it was the first time we relived it.
“You don’t want to watch it back, but we know how important it was, going into the World Cup, that we had to go back through it to come out stronger.”
On a more lighthearted note, Eric Dier is hoping for another blast of Southgate’s “karaoke tunes” after England’s World Cup semi-final against Croatia.
While Love Island and Fortnite continue to dominate down-time in the team hotel in Repino, Southgate and his backroom team are in charge of the playlist when the team bus returns victorious from the airport.
Southgate could not recall the selection he and his coaching staff put together for the team after Saturday’s quarter-final win over Sweden, but Dier had his own take.
While he was unable to identify specific tracks – blaming a combination of low decibels and generational divide – the experience clearly left an impression.
“I don’t know if they’re embarrassed about their music or the speakers are bad... it’s quite hard to hear at the back of the bus,” he said.
“They don’t put the volume up very loud – they try to keep the volume enough so that only they can hear it. But they like a lot of their, I call them karaoke tunes. Ones you can sing along to, old school Eighties and Nineties.
“There are some good ones in there, the players enjoy listening to them too, they’ve had a few singalongs on the way back from games and hopefully that will continue on Wednesday.”
Dier earned a place in the history books when he retained his composure well enough to slot home the winning penalty against Colombia in the last-16 tie eight days ago for a rare England shootout triumph.
“I think a lot of the work that we’ve done with her has been prior to the tournament starting, the last six or seven months,” he said.
“Lots of the groundwork was done then. She’s helped us in the same way throughout the whole tournament, it’s never changed depending on how far we’ve come or depending on the magnitude of the games.”
“Everything we’ve done, not just with Pippa but in general, just making sure we’ve just had consistency throughout... I’m sure that’s really helped everyone and helped keep a really good environment within the camp.”
Dier’s Tottenham team-mate Dele Alli is also appreciative of her efforts.
“She’s done a lot of work with us, more so leading into the World Cup before we got out here. She’s an amazing person,” he said.
“You can see how hard she works and she really knows what she’s talking about. She’s helped us a lot. She’s done a lot of stuff with us, takes a lot of meetings. Everyone listens to her when she talks.”
Alli did not say whether Grange had cast her psychologist’s eye over his lengthy list of pre-match rituals.
“I have a lot of superstitions. There are so many,” he admitted.
“I do all my right leg first, then all my left leg. I have an eight-minute ice-bath the night before. I don’t know why - it’s just a superstition.
“I always say a prayer, the same prayer, before. You might’ve noticed there’s tape on my knee now. That’s a superstition as well - I don’t like taking it off.
“I took it off for the first game (against Tunisia) - this is a bit of a silly superstition - but the first game here was the first game in ages I haven’t had it on, and I got injured, so I’m going to be keeping it on again.”