History awaits as Ascot United and Maidenhead United tackle FA Cup challenges

Leah Littlechild. Photo: David Bell (supplied by club)
Leah Littlechild. Photo: David Bell (supplied by club)

Maidenhead United and Ascot United go into their respective men’s and women’s FA Cup ties at the weekend with a faint whiff of history in the air.

Ascot United Women – top of the Southern Region Women’s League Premier Division and gunning for promotion to the National League – make the short trip to Brentford with a place in the Adobe Women’s FA Cup Second Round for the first time as the carrot.

Maidenhead meanwhile are aiming for a first visit to the Emirates FA Cup Second Round for the first time in the post-war era.

The Magpies record in the men’s competition in recent years leaves something to be desired but they may sniff an upset with visitors Crawley Town struggling in EFL League One.

Beth Lloyd and Leah Littlechild (pictured) top the Yellas FA Cup goalscoring charts this season with three each across a 5-0 win over Denham United and an 8-2 victory against division rivals and neighbours Woodley United.

The Yellas own match preview by Neal Jeffs has a plethora of info including: “Interim Manager Andy Cox’s side are in fine form themselves – topping the Step-five Southern Region Women’s Football League after an unbeaten start – and are bidding for a place in the Second Round Proper for the first time in their history. This Sunday’s first round proper comprises 58 ties and includes teams from the Step-three National League to Step seven regional leagues. The 58 winners will advance to the second round proper, and the 29 winners of those ties progress to the third round when clubs from the Step-two Championship enter.”

Ascot will certainly be favourites going into the game. Brentford lead the London & South East Regional Women’s Division One but are a division below the Yellas who top their own division.

Related: Women’s County Cup Quarter Finals offer pathway to silverware for Ascot, Maidenhead and Reading

Maidenhead United celebrations during an Oldham Athletic fixture. Photo: Darren Woolley.
Maidenhead United celebrations during an Oldham Athletic fixture. Photo: Darren Woolley.

Maidenhead have become accustomed to FA Cup First Round Proper dates in recent years, especially since the club’s elevation to Vanarama National League Step 1 status in 2017 meant the Magpies start in the Fourth Qualifying Round.

They may have won one of the earliest FA Cup matches back in 1871 (2-0 versus Marlow since you ask), but reaching the Second Round has proven an insurmountable hurdle for Alan Devonshire’s side who have played in six First Round ties in the last seven seasons. If we were being fair though, those hurdles have often been the likes of Portsmouth, Coventry City and Rotherham United.

Somewhat ironically, one of the club’s most memorable moments in recent years was in the 2016/17 season and began in the Second Qualifying Round culminating in a 3-1 replay defeat to Port Vale in the.. you guessed it.. First Round.

Ascot United in the 2024/25 Adobe Women’s FA Cup

Second Qualifying Round: 5-0 vs Denham United
Third Qualifying Round: 8-2 vs Woodley United

Maidenhead United in the 2024/25 Emirates FA Cup

Fourth Qualifying Round: 1-1 vs Taunton Town
Fourth Qualifying Round Replay: 3-0 vs Taunton Town

Weekend FA Cup fixtures

Maidenhead United host Crawley Town at York Road on Saturday (3pm), Ascot United travel to Bedfont Sports and Social Club to face Brentford on Sunday (3pm). A full list of all the weekend fixtures is here.

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