Break On Through (to the other side)?
07.09.26, 13:00 Updated 09.09.26, 12:20
Aynsley Taylor
No matter how many times this competition changes its name, Orient’s record has remained thoroughly underwhelming down the years. What was initially known as the Football League Cup began in 1960, and it has long been the third most prestigious domestic competition after the League itself and the FA Cup.
To be fair, we got off to a decent enough start, reaching the quarter-finals the third time it was held, which also happened to be during our only ever season in the top flight. But since 1962 we’ve failed to make it even beyond the third round, and have only managed to even get that far twelve times in over sixty years. There can’t be many clubs that have been eligible for the competition as much as we have with such a dismal record.
These days, the third round is when the really big boys join in, so it was disappointing when we pulled out Bradford City at home, a disappointment likely shared within the Club itself given their struggle to sell discounted tickets for the two stands open to home fans. And yet this tie is a great opportunity for Richie Wellens and his team to make Orient history by taking us into the fourth round for only the second time ever, and revive the prospect of a genuinely mouthwatering tie with a glamourous opponent or a visit to an unfamiliar stadium. Before last week’s visit to Bromley, Wellens remarked that his “remit this season is to have a good cup run because we need the money” so we expect to see him field a strong side, in contrast with his approach at this stage two years ago.
Six of Orient’s eleven previous forays to the third round happened in the Ear’s lifetime, so we took a stroll down memory lane to look at those and how that glass ceiling kept getting the better of us. As it turns out, although our wretched history in this competition means it isn’t held in high regard in E10, our third round exits have often involved drama and moments of historical significance.
1988: Ipswich (A) 0-2
Sponsors: Littlewoods – starting out as a sports betting company, they later diversified into retail and were pretty ubiquitous on British High Streets in the 1980s. After failing to adapt to the advent of the internet, they folded in 2005 after many years of losing money. The name has since been bought out of bankruptcy by some totally unconnected people, just like Meyba. For all those reasons, a very appropriate sponsor.
For overcoming Division Two Stoke City on penalties at the old Victoria Ground after a topsy-turvy two-legged second round tie ended 3-3 on aggregate, our ‘reward’ was a mid-week trip to Ipswich Town, also two tiers higher than Orient. Although we went on to gain promotion in May, we were struggling in 16th at the time of this game, and had lost 1-0 at Doncaster just a few days earlier. The grumpiness among the 1,000 in the away end at Portman Road was not helped by Ipswich’s young home-grown striker Jason Dozzell running rings round our defence as the home team breezed past an Orient side that put in an honourable shift but created next to nothing.
1990: Crystal Palace (H) 0-0; (A) 0-2
Sponsors: Rumbelows – by now losing millions every year, this electronics retailer went out of business 5 years later. Another great bit of foreshadowing for football.
Restored to the third division the season before, Orient had already played four games in this competition to reach this stage, and two more were required to find a winner in this tie. As a measure of how seriously this competition was taken before the Premier League arrived to start sucking life out of the pyramid, as since 1988 the first two rounds were home and away two-legged affairs, and replays were required to settle draws later in the tournament.
The first game was at Selhurst Park, and the previous season’s defeated FA Cup finalists put out a very strong side with recent knockout pedigree. So the travelling fans were delighted to come away with a 0-0 draw after centre-backs Keith Day and John Sitton absorbed everything Wright, Bright and pals threw at them. Eight days later, the replay at Brisbane Road followed a very similar pattern, with defences in command – Danny Carter in particular frustrated by Palace’s Eric Young – before the extra quality of the aforementioned Palace strike partnership eventually made the difference when Ian Wright crossed in the last minute of the game for the Mark Bright to head in the only goal after three hours of play. We’ve only met Palace once more since this encounter: another defeat in the 2001 edition of this competition (second round, naturally).
2011: Blackburn (A) 2-3
Sponsors: Carling – the final boss of taste-free gassy cooking lagers, amazingly still with us despite the quantum improvements in English beer over the intervening years. A reasonable fit for football as it still seems to be fuelling a lot of the “first pint?” antics of those incels for whom a day out at football is the only time they escape their parents’ basement.
21 long years passed before we reached the heavenly heights of the third round again, and 30 years had gone by since we’d last been to Ewood Park, during which time Rovers had become English Champions. Even though our hosts were still a Premier League side at this time, only a few hundred Os made the long midweek trip to see Jason Roberts send Lee Butcher the wrong way when rolling in a penalty late in the first half. Although Rovers dominated possession, the Os made a very good account of themselves throughout, and Russell Slade’s side not only offered a threat, but were able to make good on it twice, through David Mooney’s adroit equaliser and Dean Cox’s late goal which kept the hosts on their toes until the very end.
2014: Sheffield United (H) 0-1
Sponsors: Capital One – these American moneylenders were still relatively new entrants to the UK market at the time, and had long used sport and football clubs to raise their profile. They have an extensive history of sharp practice, but given they are currently embroiled in a dispute with Donald Trump over their closing hundreds of his accounts when he lost the Presidency in 2021, we will begrudgingly give them a pass.
We reached this stage courtesy of Russell Slade’s last great hurrah as Orient Manager, when we beat Villa on their own ground in the previous round. A solitary early goal for the Blades was enough to see us off on an occasion fraught with emotion as Slade’s tenure in E10 came to a sad end with the autumn evening closing in – one of Orient’s great modern-day Managers admitting after the game that his move to Cardiff was close. He resigned the following day, and we had nearly three more years of Becchetti to suffer.
2020: Tottenham Hotspur (forfeited)
Sponsors: Carabao – a Thai energy drinks company foisting another product with questionable effects on the nervous system onto us. Not a particularly fashionable brand, but now also diversifying into lager - so impressionable football fans will be an enticing target for them. They have impressive longevity, having sponsored this competition for a decade now, so maybe there is something to the product after all.
A particularly shameful episode in our Club’s history, requiring Nigel Travis (loyal to a fault) to circle the wagons and convince a lockdown-traumatised fanbase that this forfeit was down to the caprice of the EFL - in the face of abundant evidence that it was because of the Club’s own blunder.
The week before this game was due to take place, Head Coach Ross Embleton gave a series of interviews where he admitted that large numbers of the squad were suffering with a mystery illness but had continued to travel together, work and mingle in the midst of a global pandemic whose characteristics were very well known. The Guardian later revealed that we had suffered the largest outbreak of any professional sports club in the country and the forfeit cost the Club a six figure windfall at a time when it was unable to bring in matchday revenue, as well as the possibility of a further big payday if we’d won and faced Chelsea in the next round.
INTERVIEW: Ross Embleton post-Plymouth as Orient
2024: Brentford (A) 1-3
There were spasms of excitement around East London when this tie was pulled out. The two clubs had been on widely divergent paths in the decade since our previous (unhappy) meeting, and this was our first ever visit to a stadium that those running Orient at the time held out as a model for our future. Richie Wellens seemed entirely unbothered by the prospect of winning this tie and making history, fielding a mostly second string side to the frustration of fans who relished the prospect of getting one over on Brentford in their new back yard.
Brandon Cooper triggered jubilation in the away end with his early goal, but our top flight opponents had too much for us on the night, even though they were giving their own second string a run out. It was an edgy night in the stands, with aggressive stewarding further aggravating an already rowdy away end. The brother of a senior Club official was caught up in the ruckus as the second half began and ended up spending a night in the cells after a contretemps with plod, although thankfully no charges were brought.
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Aynsley Taylor Editor of the Ear since 2021, and proud to take it into its fifth decade. Was singularly unqualified for the job, but no-one else wanted to do it. Sees Orient with the zeal of the adult convert rather than someone who was dragged to church every weekend from childhood.




