First Richie Wellens and now experienced Doncaster Rovers team-mates Paul Keegan and Richard Chaplow have been busy passing on nuggets of advice to the talented 20-year-old in the heat of battle.
Not forgetting managerial duo Darren Ferguson and Gavin Strachan, both engine-room operators in their playing days who have been helping to fine-tune Middleton’s game at the club’s Cantley Park training ground.
The tough part is taking on board that tutelage and striking out on your own. The smart money is on all those who have Middleton’s best interests in hearts not needing to bend his ear for too much longer.
Middleton’s progress from rookie to fully-fledged first-team regular is fairly well down the road and is helping to mitigate for the departure of veteran Wellens, a player that the lad from Hatfield Woodhouse looked up to.
Middleton has emerged from Wellens’s shadow impressively and another test will come this afternoon in a home derby with Sheffield United which has the portents of a somewhat tense occasion given both side’s acute need for a positive result.
Given his development this term in a breakthrough year which has seen him make 29 appearances, few would bet against him rising to the challenge.
Middleton told The Yorkshire Post: “Obviously, I was second in line when Ritchie was here. But there’s still the likes of Keegs and Chaplow and I am learning off them as best as I can.
“They all try and push you as best as they can and I try and give it back, too.
“But I have a little bit more responsibility now.”
On the specific input of Rovers’ managerial team, he added: “The gaffer and Strachs have helped me massively.
“Since they have come in, I think I have personally come on a lot.
“There are a lot of things I don’t think are necessarily wrong, but that they think I can improve. It’s little things they tell you that just help your game massively and give you more time and space.
“They have looked at my game and picked individual things for me to do better.
“I’ve been working on mainly body shape and getting on the ball, rather than chasing the ball. It’s about staying away from the game a little bit and giving myself a little bit more space to move it quicker. They have also worked on me switching play.”
The investing of so much faith by Ferguson and Strachan – and others – in the development of Middleton is a real barometer of how highly that boyhood Rovers fan is rated by those in the know at the Keepmoat.
The evolution of the young midfielder, who was the club’s development squad captain last term, has been refined during a breakthrough campaign, which has seen him take responsibility, mature physically and find his voice on the pitch.
He is the first to admit that he is by no means the finished article, with improving his goals ratio being a clear box to tick, but the likelihood is that they will arrive in time.
He added: “This season was big for me to break in as best I could.
“Personally, I think it has gone well for me. Obviously, before the season, I was aiming to be involved more than last time and I have been involved a lot more than I anticipated, which has been really good.
“Performance-wise, I think I have got better as games have gone on. I just think I just need to add more goals and assists to start affecting games more.
“But it is the first season where I have felt part of a team rather than a young lad coming in. I am hoping that is showing.
“I am more confident in my own ability really. Whereas a year or two ago, I was just holding back a little bit as I wasn’t sure if I could cope or play well.”
As someone who used to watch Rovers from the terraces as a youngster at Belle Vue, when the derby fare included the likes of Scarborough, York City and Mansfield Town, he appreciates that having the Blades as local rivals has moved things to a different stratosphere.
While Rovers have aspirations down the line to return to the second tier following two spells there in their recent history, the pressure on the Blades to end their own Championship exile is of the heavy-duty variety.
Now in their fifth campaign in League One, the Bramall Lane outfit’s penance at this level has been a wholly excruciating one for Unitedites.
The Blades’ massed followers at the Keepmoat this afternoon need no reminding of their ignominious position of 11th and neither does manager Nigel Adkins either.
If they are to somehow end their stint in League One, you sense much of it will be down to a man Rovers know well in Billy Sharp, who proved a big crowd favourite during his productive spells at the club.
Not that Rovers will be wanting to witness too much of the Sharp prowess today.
Middleton said: “Sheffield United are a massive club who will be disappointed where they are. They have got some good players and a big fan-base. They should be up there.
“Their main player is Billy Sharp and he’s been here a long time and everyone knows what he’s about. He scores goals and even if he is not playing brilliantly, he is always a threat throughout.
“If you switch off for half-a-second, he’s is going to punish you and is probably their main threat.”