There are certain young players who gradually make their way into the first team and before anyone has really realised they become an established member of the side.
In the club’s last Europa League clash, Middleton was introduced after Villarreal had just scored their second goal of the evening to make it 2-1.
After a frustrating evening in which Steven Gerrard’s side had looked clumsy and erratic on the ball, Middleton took on the Spanish defence with purpose and a direct style that had been sorely missing all night.
The youngster had faced Valencia’s youth team in February and knew that if he could match the pace of a Spanish full-back, he wouldn’t have to worry about being knocked off the ball.
And as such the young lad from Glasgow set about tormenting Miguelón on the Rangers left flank for the final 20 minutes of the game.
And, six minutes after coming on, he made a decisive impact. His perfectly-weighted through ball found Borna Barisic, whose cross was met by Kyle Lafferty at the front post. The striker glanced his effort into the net and Rangers clinched an important European result.
The cameo was, undoubtedly, the highlight of Middleton’s senior career to date, yet one would forgive the youngster for hoping to eclipse it at some point soon.
After all, he only joined Rangers in January and it wasn’t until Gerrard showed up at Ibrox in the summer that fans finally got to see who their club had pinched from Norwich City’s youth academy. So far they’ve been hugely impressed.
Although the youngster hasn’t started a game for Rangers in the league or Europe this season, he did take advantage of such an opportunity in a recent League Cup quarter final against Ayr United, when he scored two and assisted the third of the team’s four goals that day. He was given a chance and he took it in style.
In a similar vein to Scottish wideman before him, such as Aiden McGeady or Shaun Maloney, or perhaps even former Rangers wing-back Alan Hutton, Middleton excels in his ability to break with incredible acceleration coupled with a low centre of gravity that allows him to turn with remarkable precision.
The 18-year-old may be 5ft 9ins, but he looks far shorter when hunched over the ball and seemingly squeezing past opposing defenders with relative ease.
In the summer Gerrard brought in three players that can play on the left wing in Scott Arfield, Ryan Kent and Lafferty. Add that to Jamie Murphy signing in January and there is genuine competition for Middleton.
But, due to a long-term injury to Murphy, Arfield’s move in to central midfield and Lafferty playing as a more traditional No.9, the Glasgow-born talent has been left to challenge Kent directly for the left wing spot.
To the noted appreciation of the Ibrox faithful, Middleton has lunged at such an opportunity and while Gerrard may have certain obligations to play Kent while he’s on loan from Liverpool, he rarely misses a chance to throw the 18-year-old into the action.
Whether the winger will have to take a step back when Murphy returns from injury remains to be seen. But in 11 appearances for the club, Middleton hasn't put a foot wrong.
It wouldn't be a surprise, before too long, to see the Glasgow talent pushing for a regular spot in Gerrard’s side, irrespective of the other options available to the Rangers manager.