Cheltenham Town faces 2021 winners Leicester City in the FA Cup third round at a packed EV Charger Points Stadium this Saturday, with kickoff scheduled for 12.15pm. Despite the excitement, these clubs have only crossed competitive paths twice, both times during the 2008/09 League One season, with Leicester emerging dominant, winning 4-0 in both games.
That season saw Leicester City under Nigel Pearson’s guidance storming to the League One title, amassing an impressive 96 points and finishing seven points clear of runners-up Peterborough United. Meanwhile, Cheltenham Town endured a difficult campaign, finishing 23rd and facing relegation to League Two, narrowly above Hereford United.
Cheltenham’s home encounter at Whaddon Road came early in the season – their fourth game – following a tough 4-0 defeat at Oldham Athletic. Keith Downing’s tenure as manager was soon to end. The match was tight at halftime, with Lloyd Dyer’s opener giving Leicester a 1-0 lead. However, after the break, Matt Oakley, Matty Fryatt, and Dyer added goals to complete the 4-0 triumph in front of 5,344 fans, propelling Leicester to the top of the table.
READ MORE: Former Cheltenham Town Forward Harry Williams Signs with Bishop’s Cleeve
READ MORE: Police Officer Dismissed for Sexual Harassment of Female Colleagues
By the return fixture at the Walkers Stadium, Martin Allen had taken over as Cheltenham manager. Allen had a past connection to Leicester, having briefly managed the Foxes at the start of the previous season for just four games. At that point, Cheltenham was struggling, on a 15-game winless streak. Yet Leicester once again ran out 4-0 winners, with goals from Steve Howard, Fryatt, Tom Cleverley, and Oakley. The match was witnessed by 18,939 supporters.
Cheltenham had previously played at the Walkers Stadium in a behind-closed-doors friendly in July 2007, losing 2-0 to goals from Fryatt and Darren Kenton, who would later join Cheltenham. Remarkably, the return leg of the 2008/09 season was originally scheduled for Whaddon Road, where Allen’s father Denis had managed in the 1970s. However, severe flooding in Gloucestershire resulted in no running water at the ground, forcing the match’s relocation.
Since then, the clubs have met in a high-profile friendly in July 2019. Brendan Rodgers brought a strong Leicester squad, including stars Harry Maguire, Youri Tielemans, and Jamie Vardy. Cheltenham’s Leicester native, Luke Varney, gave the Robins an early lead with a header, but Vardy and Marc Albrighton secured a 2-1 victory for the Foxes at Whaddon Road, in front of 3,707 fans, including 1,224 visitors.
Leicester City’s first ever floodlit match was hosted at Whaddon Road in March 1952, a friendly arranged as part of Peter Rushworth’s transfer to Leicester. Rushworth captained the Foxes against his former club. Leicester’s Combination team won 3-1, despite an outstanding performance from Cheltenham’s goalkeeper, Ron Coltman. The Leicester Evening Mail remarked positively on the floodlighting, with manager Norman Bullock noting he could “follow the match perfectly.” Though centre-half Reg Halton admitted the lights caused some difficulty when the ball went into them, overall visibility was good.
In more recent times, Cheltenham defeated Leicester Under-21s 6-1 at home in the EFL Trophy in January 2017, with Diego De Girolamo netting a hat-trick. Other goal scorers included Daniel O’Shaughnessy, Billy Waters, and Amari Morgan-Smith. Leicester’s sole goal came from Bartosz Kapustka. The Foxes featured promising talents such as Hamza Choudhury and Josh Debayo, the latter joining Cheltenham in 2018.
Leicester’s Under-18 squad also bested their Cheltenham counterparts 5-0 in the FA Youth Cup third round at the King Power Stadium during the 2015/16 season. Players like Cam Pring and Luke Thomas, who now play for Bristol City and Bristol Rovers respectively, were part of Jamie Victory’s Cheltenham lineup.
Cheltenham Town and Leicester City’s sporadic encounters reflect a history shaped by floods, floodlights, and footballing highs and lows — a distinctive chapter in both clubs’ stories.