Steve Guppy is the one everyone remembers. Most dedicated followers of English football in the late 1990s and early 2000s would also be able to name Jason Wilcox and Steve Froggatt. Then you have your David Dunns, your Alan Thompsons, your Chris Powells. Two decades on, the infamous “England left-sided problem” tends to be evoked more as an exercise in nostalgia, a display of performative recall, than as a long-term failure of systems and imagination that Gareth Southgate may just be in danger of repeating.
A “left-sided David Beckham” was Kevin Keegan’s memorable description of Guppy ahead of his England debut, which sadly would also turn out to be his England swansong, against Belgium in 1999. And over the years, as the tournament failures piled up, England’s problem left flank would become a sort of hex, a footballing black hole, a lost cause to which some of our best young men were sacrificed, not all of whom would survive the experience.
There were the hopeful Premiership journeymen such as Guppy and Wilcox. The utility midfielders like Kieron Dyer, Trevor Sinclair and Nick Barmby. Then there were the desperate punts: Dennis Wise at Euro 2000, Emile Heskey at the start of his England career, Paul Scholes towards the end of his. Through it all, nobody seemed to grasp the most elegant solution: if you don’t have the players to play the system, change the system. Instead, as late as Euro 2012 England teams were still cleaving faithfully to 4-4-2 as if mandated by some long-forgotten Elizabethan by-law.
Ultimately, the game itself would change long before England did. The switch to two-bank midfields and a greater emphasis on attacking full-backs, coupled with the emergence of Ashley Cole as England’s first genuinely world-class left-sided player since Chris Waddle, jolted them into a painstaking evolution. And yet, as England prepare to embark on the final leg of their international week, it is tempting to wonder if Southgate is beginning to encounter a new strain of an age-old problem.
The withdrawal of Ben Chilwell and Kieran Trippier from the squad to face Denmark at Wembley on Wednesday night has again left Southgate short of options at left wing-back: a stark contrast to his abundance of riches on the right. His choice will likely be between Bukayo Saka, who fulfilled the role competently enough against Wales last Thursday, and his Arsenal team-mate Ainsley Maitland-Niles, who is right-footed but has fleetingly played at left-back in the past.
The pitfalls of playing a right-footer on his weaker flank were manifest during the sluggish first half against Belgium on Sunday evening. Trippier has acquitted himself well in deputising for Chilwell this week, but even so the lack of a natural left-footer gave England’s attacks a lop-sided feel, effectively narrowing the pitch and making them easier to defend against. Marcus Rashford, on the left of England’s front three, frequently found himself marooned to the wing: no overlaps, no overloads, no decoy runners, and no options. Forty of his 59 passes on the night went backwards.
With Southgate committed to playing a 3-4-3 against strong opposition, the need for genuine width, for a player who can get to the byline and make crosses, is manifest. The identity of that player, on the other hand, is more open to conjecture. Unlike Scotland, who boast not only Andy Robertson but Kieran Tierney, England are not blessed with options in this department.
After the reverse fixture against Denmark last month, a 0-0 draw in Copenhagen in which Trippier was again assigned to the left flank, Southgate was asked whether a left-footer might be better suited to that position. “Where is that player?” Southgate demanded. “I keep hearing that argument, but I think Kieran has had two excellent games for us.”
Chilwell, who has started brightly at his new club Chelsea, is still the man in possession. Yet his absence from these three fixtures – due initially to a breach of coronavirus protocols, and now to injury – has set his cause back. Meanwhile the emergence of Saka, who has played both at left-back and in midfield under Mikel Arteta at Arsenal, should at least offer some viable competition. Quick, hard-working and able to cross on the run, Saka now has a chance to make the shirt his, even if his defensive positioning still occasionally lets him down.
Beyond those two, however, the picture looks bleak. Injuries and loss of form have sent Luke Shaw’s career into decline. Danny Rose looks like a sketchier and more pallid version of the player he once was at Tottenham. Aaron Cresswell and Ryan Bertrand are both sturdy if unspectacular alternatives. Doubtless Southgate will be tracking the progress of Rico Henry at Brentford and Ryan Sessegnon at Hoffenheim as longer-term options.
And really, this is an issue that goes wider than one problem position. England lack left-footers in virtually all areas, even if most of their wide players can generally take the ball both inside and outside. Rashford and Jack Grealish, the two leading contenders to start on the left flank against Denmark, are both right-footers who like to carry the ball inside. In defence, Tyrone Mings owes his place largely to being one of the only decent left-footed English centre-backs in existence.
Meanwhile, in a rich irony, the Icelandic transgressions of Phil Foden and Mason Greenwood have deprived Southgate of probably his two best left-footed attackers. A reminder, if needed, that an uncomfortably large part of international management comes down to pure, stupid chance.