“He just told me to go out and give their right-back pure hell,” grinned the teenage winger who, it’s fair to say, did his level best to fulfil his manager’s wishes.
Middleton, having already earned the approval of the Rangers support with glimpses of his ability during a series of substitute outings this season, lit up the 4-0 Betfred Cup quarter-final win over Ayr United at Ibrox as he scored twice in his first full 90 minutes of first team action.
The Glasgow-born boyhood Rangers fan certainly did enough to suggest he can emerge as much more than just an impact player from the bench.
Middleton is something of a throwback as a wide man, utilising pace and directness with a simplicity which can be devastatingly effective as the Ayr defence discovered to their cost.
“I’m always going to go at someone and that’s just what I do,” said the 18-year-old. “I’m not going to say I am the most technical player in the world because I’m not. I’m just lucky to have good players in this team who help me out and I have been lucky the manager has been really good with me
“He has been brilliant since day one, it’s been a dream come true for me to get into the first team under him. The players and the rest of the staff have all been very, very good with me as well.
“I’m confident going into any situation now because I know I’ve got the standard of player around me in different positions to give me the chance to do what I can do. It’s up to me to keep taking my chances whenever I get them.
“It’s just the case of taking the chance to show the manager can trust me in any situation. Everything just adds up. I keep doing things bit by bit and it seems to be going in the right direction at the moment.
“The fans have been great with me every time I’ve been on the pitch. I’m very grateful for their support and so hopefully, when I do get the chance, I want to repay them.
“I was really happy with how it went against Ayr. But it’s not about me, it’s about the team and the object was to get into the semi-finals.”
Middleton is a legacy of Graeme Murty’s second spell in charge of Rangers, having worked under the academy boss at Norwich City who allowed him to move north on transfer deadline day back in January this year.
Capped at every level for Scotland from under-16 to under-21, Middleton now hopes to have nailed down a regular place in the starting line-up by the time next month’s semi-final against Aberdeen comes around.
“It would mean everything to me to be involved,” he added. “I am as desperate as anyone to get this club back and winning a trophy. But we will need to see what happens.
“We have a really good squad now and I think everyone can see that. We have got two or three top players in every position. So it’s up to us to give the best performance we can whenever we get the chance.
“Wednesday showed we are definitely going in the right way. There were a few changes to the starting line-up, me included, and I think we all showed we didn’t let the levels drop too much. Everyone in that squad knows what we are capable of doing. It’s just about making it happen.”
With Alfredo Morelos suspended and Kyle Lafferty ineligible, front line places will certainly be up for grabs in the semi-final as Middleton looks to press his claims over the coming weeks.
“Everyone has got their own case to make for a place in the team,” he said. “It’s just about us doing our own bit in training and giving the manager a decision to make.
“I actually played as a central striker when I was younger – it was my position and like any forward I love scoring goals. It was great to get the two goals on Wednesday, although I need to work on my goal celebration because the second one didn’t exactly go to plan.
“I also had a good chance to get my hat-trick but I got a little bit too excited and just rushed my first touch.”