On Wednesday morning, I was gearing up for another write up about transfers, with the deadline looming large this coming Monday. However, the events in the Carabao Cup that evening changed everything.
Grimsby 2-2 Manchester United (12-11 on penalties) is possibly the greatest cup-set in history - we’ll unpack why later. Within half an hour, Grimsby Town were 2-0 up, with goals from Charles Vernam and Tyrell Warren, and things were looking dire for Manchester United. Thankfully, they were able to bring a host of first-team substitutes: Bryan Mbeumo, Bruno Fernandes, and Matthijs de Ligt entered the pitch.
It wasn’t all bad for Manchester United - at 60 minutes, Ruben Amorim got out the tactics sheet, and by 90, the score was 2-2, with some very embarrassed celebrations from Mbeumo and Maguire after their goals.
For my money, one of the best things about the Carabao Cup is that games go straight to penalties, and extra time is scrapped. Extra time disproportionately stacks the odds in favour of the team higher up the pyramid, and their stamina often tells (see Tamworth v Tottenham in January 2025, where 0-0 after full time became 0-3 after extra time). Penalties are meant to be the great leveler… in theory at least.
We’ve seen long shootouts in this competition before: Preston North End 16 - 15 Fulham saw 34 (!) penalties be taken, with only a couple of misses throughout the shootout. And it certainly felt interminable for Grimsby v Manchester United last night. Both keepers managed to save one penalty during the initial five, and then the shootout went to sudden death. Even as the tension rose, both teams slotted their penalties away with ease, until this moment…
One hilarious note about the shootout is that Manchester United’s star £73 million striker, Benjamin Sesko, was the tenth United play to take to the spot - behind every defender and other midfielder, and only in front of the goalkeeper. Manchester United’s £73 million striker.
In the end, Grimsby were victorious, and celebrated with a pitch-invasion. Unless you’re a Manchester United fan, you can’t help but smile.
Cup-sets - a lower league team knocking out a giant - feel unlikelier these days - sometimes they feel like a bit of a myth. The Tyne and Wear derby of January 2024 is a perfect example of this: Sunderland of the Championship were raring to go and primed for an upset, but they were totally outclassed, 3-0, by their Premier League rivals Newcastle. In the same month, West Brom were up for a derby against their local rivals, Wolves, and it was a similar story - a comprehensive 2-0 win for the Premier League side.
The wealth disparity between Grimsby Town and Manchester United - between any lower-league team and a Premier League team - is huge. Grimsby’s squad value is £3.1m and Manchester United’s squad value is £769m. In May 2025, Forbes pronounced Manchester United to be the second most valuable club on the planet, only behind Real Madrid. Grimsby (obviously) didn’t feature on the list. This kind of financial disparity has only widened over the years, with the richest clubs growing exponentially richer.
This is almost the perfect cocktail of ingredients to make it the greatest cup-set of all time: Grimsby going two up before being pegged back, the interminable penalty shootout, and the huge (and ever-growing) gulf between the teams financially. More than that though, the internet’s reaction to the defeat has been delicious, from the memes of Amorim with his tactics board, to the United Strand’s video from the shower (for those unfamiliar, Frank Ilett is not cutting his hair until Manchester United win five games in a row - and it’s not looking good).
Round 3 will hopefully feature some more cup-sets, as the teams playing European football enter the competition. Will Port Vale be able to surprise Arsenal, or will Huddersfield manage a surprise win against Manchester City? One thing’s for sure - it’ll have to be pretty special to beat this one.
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