It’s the question that gets asked throughout the FA Cup every single year.
The lowest-ranked remaining team in the FA Cup, in whatever round, always has a special spotlight shone on them. Clubs ideally want to be drawn against them and simultaneously almost everyone else wants to see them win their next game.
As England’s famous domestic competition progresses, the lowest-ranked team tends to get knocked out and a new underdog takes centre stage, until invariably one of the big teams wins the tournament. It is not always that simple, and perhaps this will be the year when a non-league side gets to Wembley.
For the fourth round of the 2023/24 FA Cup, Maidstone United are the biggest underdogs left still standing. They play in the National League South, the sixth tier of English football.
Having reached the fourth round, Maidstone United are currently enjoying the best FA Cup run in the club’s history. The Stones reached the third round proper in 1983/84 and 1986/87 but were beaten by Darlington and then Watford.
Maidstone have also made it to the second round on five different occasions, the most recent being the 2019/20 season where Blackpool beat them 3-1. The change in quality of opponents can be stark in the second round and that is where so many of the last non-league teams are eliminated.
As a National League South side, Maidstone United’s FA Cup journey started in September in the second qualifying round. They were away at Steyning Town to begin with and comfortably won that game 4-1.
That set up another away trip in the third qualifying round, this time against Winchester City. They also cruised through that clash, winning 2-0 at the end of September. Torquay United were next, with a place in the first round proper on the line. Another 2-0 away win set up yet another away tie against Chesham United, which also ended 2-0 to Maidstone.
Getting to the second round inevitably came with a game against a side at least one division up and they ended up being drawn at home to Barrow, currently fourth in League Two. There is a big gap between the two sides, but a 74th-minute winner from Bivesh Gurung ensured a 2-1 win and a place in the third round.
Sam Corne scored Maidstone’s equaliser against Barrow and stepped up to the penalty spot against League One’s Stevenage in the third round. Both Sol Wanju-Smith and Jacob Berkeley-Agyepong tumbled inside the opposition box in the same forward thrust…
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