On Tuesday night, Rangers progressed through to the final of the Glasgow Cup.
An U20s side defeated Queen’s Park 1-0 at the Hummel Training Centre.
However, it was far from a straightforward encounter and Graeme Murty’s side was forced to work for their victory.
The winger was lively from the off and tested out the opposition keeper on multiple occasions in the first half.
Shortly after the break, he came agonisingly close, hitting the crossbar with a well-struck effort.
Therefore, opportunities were limited, while those that did materialise, went a-begging.
However, just as the game looked destined for penalties, Nathan Young-Coombes made an impact.
— Rangers B & Academy (@RFC_Youth) February 1, 2019
Middleton then stepped up and duly converted under pressure from the spot.
It capped a fine individual display and brings more success at age-group level, setting up an exciting Old Firm final.
With the ex-Norwich man currently frozen out of the first team, this display is a timely reminder for Gerrard of his capabilities.