Or, if not this evening, then against Kosovo on Sunday. If England travel to Pristina with their place at the tournament already assured, Maddison will almost certainly receive his first cap.
Which is interesting, because Gareth Southgate has moved carefully around the Leicester City midfielder, seemingly suspicious of his image, his attitude and how those qualities might clash with the squad’s incumbent personalities.
Southgate has reason to be cautious. Maddison withdrew from the last England squad because of illness, only to be photographed in a casino that same night. He has kept his place in spite of that, but with a warning ringing in his ears.
“You want to be high-performance, low-maintenance”, Southgate told the press at the time. “I am prepared to work with players who are more difficult but you’re more likely to back those players if they’ve scored a winner for you and sweated blood for you, and that’s the bond you build with those players over a longer period of time.”
It’s strange for a player to have that reputation so early in his career. The specifics also seem out of time. Casinos, nightclubs; those are props from a different era of Premier League football. Like centre-partings. Like Chinawhite. They're relics from the Dean Gaffney years.
Which, in a way, is perfect, because Maddison is a bit of a throwback himself. That shows in the slightly anachronistic way he plays, with that heavily stylised ball-striking ability, or the way he shapes up to a set-piece. Most vividly, it's in his long-range shooting.
But also in terms of how he’s perceived. A bit cheeky, a bit roguish – almost a cliché of the modern player, with the typical haircut, the fashion and the swagger.
But what that portrays remains imprecise. The world is yet to decide whether Maddison is really descended from David Beckham or if, actually, that’s just a superficial likeness hiding the Bullard and Bentley DNA.
In a way, that’s terribly unfair. Part of what has made Maddison successful, or at least what eased his transition into the Premier League, was the same self-confidence for which he’s now damned. Expressive and confident has become cocky and arrogant, a happy-go-lucky character has been branded a party boy.
It’s very premature. Especially as, for the moment, Maddison is playing to a very high level. More importantly, he’s an integral part of a Leicester side who are performing outstandingly well and whose synonyms are all healthy and positive. Leicester are bright, hard-working and evidently receptive to their head-coach, and Maddison appears to be a cornerstone personality within their group.
And yet there’s something to distrust about his ability. Not its existence, but the way it might develop. For now, he’s a young player making the odd bad decision. Tomorrow he might not necessarily be Frank Worthington or Jim Baxter, but there’s still a tenuousness to his future and doubt as to whether the talent that has brought him to the England squad will multiply as it should.
More than anything, Maddison is a professional who seems to be in a productive, but precarious balance. He has just enough self-belief, his dose of confidence seems precisely right. He seems to enjoy the life of a footballer in a way that manifests in how he plays the game and that makes him as attractive to some as it does unappealing to others.
When that’s the case, any interference with those ratios is potentially dangerous.
England, clearly is one of those factors. So what does becoming a senior international do to that kind of personality – how much extra strut does that put in the step of someone who already carries himself like a star.
Will it refine his habits? Will the experience and extra status condition a mentally leaner player? Or does reaching this waypoint in spite of the occasional stray to the casino and lapse in judgement dissuade him from the need to tread more carefully in the future. Does the mountain no longer appear quite as steep?
There aren't really answers to those questions yet. But perhaps this is part of what makes Maddison such an alluring talent. It's his ability, of course, and the goals, the free-kicks and the artful passes. But it's also this curious sense of susceptibility, a glint in his eye which makes these moments within his career potentially so instructive.
While you're here, why not take advantage of our brilliant subscribers' offer? Get the game's greatest stories and best journalism direct to your door for only £9.50 every quarter. Cheers!
Get the best features, fun and footballing frolics straight to your inbox every week.
Thank you for signing up to Four Four Two. You will receive a verification email shortly.
There was a problem. Please refresh the page and try again.