Liverpool midfielder Alex Oxlade-Chamberlain faces Arsenal reunion with career at a pivotal crossroads

Unusually for a precocious talent breaking through at Arsenal during the Arsene Wenger years, the League Cup was not employed as a lower-stakes schooling ground for Alex Oxlade-Chamberlain.

Granted, the midfielder scored his first Gunners goal in the competition, in a third-round tie against Shrewsbury in September 2011, but for the most part it was straight into deeper waters for the teenager after his summer arrival from Southampton.

By then, he had already made his debut in the infamous 8-2 defeat to Manchester United at Old Trafford and would get his first Premier League start in the return fixture, when the boos that greeted his withdrawal represented some of the first widespread public dissent towards the club’s legendary manager.

A week after the Shrewsbury game, Oxlade-Chamberlain’s first Champions League appearance saw him become England’s youngest ever scorer in the competition, before, the following spring, a stunning, breakout display in central midfield against AC Milan in the last-16 truly confirmed his potential.

Yet a decade on, and with fewer than 18 months to run on his Liverpool contract, it would seem that tonight’s Carabao Cup semi-final meeting with his old club comes at a pivotal crossroads in a career that - largely thanks to rotten luck with injuries - remains unfulfilled.

There are parallels with the likes of Dele Alli, Ross Barkley and Jesse Lingard, a generation of English attacking midfielders who have all, for varying reasons, plateaued, declined or drifted through what might’ve been the primes of their careers.

Unlike that trio, however, Oxlade-Chamberlain has Premier League and Champions League winners’ medals to show for the supposedly lean years and, crucially, looks in a position to play a regular, albeit not pivotal, role in his club’s pursuit of more trophies between now and the end of the season.

Only last month, Jurgen Klopp was hailing “the best Oxlade” he has known since his arrival at the club, the midfielder afforded the kind of run of form and rhythm that has largely eluded him since he was cruelly ruled out for a year after tearing his ACL in the 2018 Champions League semi-final.

“I know he wants more spectacular in moments,” the German said, “but it is a completely new quality now – calming the game down, being not only the sprinter with the ball or the shooter but being involved in all the things on the pitch. It is a massive step.”

But such praise did not come with any guarantees about what lies ahead.

“It is about what makes sense for both sides in six or 18 months or whatever,” Klopp added. “We will not stay together forever. That is how it is.”

The Liverpool boss will have major decisions to make when redressing the balance of his midfield this summer, a balance that has seemed off since he opted against signing a direct replacement for Georginio Wijnaldum, not helped by Harvey Elliott’s horrific injury. The teenager - like Oxlade-Chamberlain, a sort of hybrid winger - having made a promising start to the campaign.

At 28, despite the injuries, Oxlade-Chamberlain remains a dynamic force, retaining a rare skill for surging through a congested midfield and a range of passing that, with an air of prescience, had Wenger comparing him to Anfield great Steven Gerrard by the age of 20.

But for a player whose goal threat is supposed to offer a point of difference compared to the likes of Fabinho, Jordan Henderson and Thiago Alcantara, a return of two goals in 40 appearances (admittedly, many of them as a substitute) since his return from another knee injury last season is nowhere near good enough.

Like a bowler beating the edge over and over without finding the all-important nick, it feels as if Oxlade-Chamberlain is forever whistling low strikes across goal and just past the corner or curling efforts inches beyond the far post, convincing you that, eventually, he’ll get his rewards.

With Mo Salah and Sadio Mane away at the Africa Cup of Nations and a return to a more attacking role - a chance to bowl with the new ball, so to speak - apparently in the offing, now would seem an opportune moment for them to, belatedly, arrive.