When you look into a club’s history, you have to look into their biggest games and most famous victories. Ask a Villa fan and they’ll mention 1982, ask a Manchester United fan and they’ll say the 1999 treble, ask an FGR fan and they’ll mention a time they beat us. While it’s true that games such as Rushden and Diamonds, Grimsby Town, Yeovil Town, and Halifax have been monumental in getting the club to where they are today, they weren’t quite the biggest teams we’ve come up against…
August 2021’s win over UEFA Cup winners Ipswich Town came as a shock to all visiting supporters and a night of jubilation for the home crowd. Ipswich were the first so called ‘big club’ to come to Whaddon Road in the 2021/22 season and the first to fall to ‘the tiny club near some horses’. With the likes of Sunderland, Sheffield Wednesday and Portsmouth all coming to town, there were plenty of chances for a big club scalp. So without further ado, I’ve compiled a list of some of the biggest wins against the biggest clubs, the highest calibre of opposition who left disappointed since our ascension to the Football League in 1999.
To preface this, many clubs’ fans seem to believe that size settles games, because they are bigger they should win automatically but as we know full well, this is not the case...
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LEEDS UNITED
Cheltenham Town overcame Leeds United not once, but twice, in League One. A source of pride for many fans of the Gloucestershire club saw the robins come away with the three points both home and away, made all the more important when you consider the fact that we stayed up by just three points at the end of the season. The first win came in November of 2007, when 7043 people were in attendance to witness Steven Gillespie’s 86th minute strike to steal a late win for the home side. The goal, which came from 30 yards out, lifted Cheltenham off the bottom of the table and left Leeds with only their second defeat of the season. The second win came in March 2008 as David Bird and Alex Russell scored to see off the promotion contenders. These were two famous days in Cheltenham’s history (which I bring up very often, taking every chance when Leeds United come into a conversation) and ones we will hope to emulate for years to come.
BOLTON WANDERERS
It may just have been in the Checkatrade Trophy with much changed sides, but it came on the ninth anniversary of the Lancashire side holding Bayern Munich to a 2-2 draw in the UEFA Cup at the Allianz Arena. A famous night for them that they had to reminisce about from the stands at Whaddon Road on a cold night in Gloucestershire. Despite the 21 shots in the game, there were no goals until the very end when Amari Morgan-Smith beat Bolton’s Ben Alnwick to the ball and was brought down in the box. Morgan-Smith himself stepped up to slot home and win the game.
It was a rare run out for the likes of Jack Munns, Dan Holman, Callum Kitscha and Morgan-Smith who struggled for game time during our first season back in the Football League. Title winning heroes were swept aside, football is a ruthless game after all, with Aaron Downes and Dan Parslow considered too poor to keep us up and Jon Flatt who many were happy to see the back of having seen him face to face while picking the ball out the net so often.
We’ve faced Bolton a few times since, with a draw the most common result and the two clubs seeming to be the same level in the modern game.
It happened again in similar fashion this week as Ryan Broom's late goal sealed a first ever league win against the Trotters after Wade Elliott's side dominated throughout, outplaying and outclassing the former Premier League club.
IPSWICH
UEFA Cup winners, First Division champions, FA Cup victors. Ipswich came into their game against the robins on the back of a poor start to the season, still looking for their first win of the campaign. Despite their poor form and lack of goals, their name alone should have warranted all three points according to some. Will Boyle thought otherwise. A goal and assist from the centre back saw the robins turn the game around after Matt Penney’s early strike. The game could have been completely out of our control had Ipswich attacker Macauley Bonne chosen to head home his lob and not side foot it in which gave Owen Evans the time to get back and keep it out. We capitalised on the poor finishing as Duff’s men took control of the game in the second half and left the tractor boys silenced by the tractor song in celebration of two title winners.
Wright’s header and Boyle’s late strike to sealed the three points. I recommend you do what I am about to do and watch the highlights just one more time. Better yet, a makeshift Cheltenham side went to Portman Road on a Tuesday night with pretty much 14 players later in the season and came away with a 0-0 draw, much to the anger of the home fans.
CHARLTON ATHLETIC
Over 500 Cheltenham fans descended upon the capital to witness a famous day in the history of the club. A team who had spent much of the 2003/04 season challenging for the Champions League places in the Premier League and who had spent eight seasons in the ‘Prem’ had fallen to Michael Duff’s men. It was a bright start for the away side who took the lead after only six minutes courtesy of Matty Blair’s slotted finish at the third attempt after Taylor Perry and Alfie May were unable to convert. Just after the half hour mark, Cheltenham doubled their lead as Blair turned provider, seeing his cross converted by Perry who put the ball past Craig MacGillivray and into the Charlton goal. Boos erupted around the ground.
Perry, Wright and May all had great chances to extend the lead but for a superb second half display from MacGillivray to keep it at two. The hosts did see some resurgence after the break, pinning Duff’s men back for much of the last 45. Substitute Jonathan Leko made it 2-1 in the 59th minute but poor finishing and solid goal keeping from Scott Flinders meant that no more goals went in and the 2-1 final score made for a great day out for the robins.
SUNDERLAND
This one was fun. After an almost 10 hour round trip to the Stadium of Light in September 2021 for a 5-0 defeat, you would be excused for expecting the worst from the return fixture. If you’ve read my stuff online, you’d know how confident I was that we would score.
It didn’t start too well when a free kick from Alex Pritchard on the half hour mark put the visitors ahead and set us up for what some thought would be a long night. The tides changed in the second half, Duff’s men started to control the match and take the game to the visitors. The breakthrough was made when Elliot Bonds picked up the ball on the edge of the box and saw his left footed effort take a very slight defection and nestle between the bar and ‘keeper’s gloves to make it 1-1. Hopes were high for a famous win and Whaddon Road soon erupted once more as Evans’ long ball to Kion Etete was played through to Alfie May who fired home to make it 2-1.
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