Josh Umerah in action at Maidstone United last week. Photo: Maidenhead United

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Maidenhead United have been drawn away to National League South league leaders Maidstone United in the second round of the FA Trophy.

A total of 40 second round ties were drawn this Monday lunchtime (October 26) with the matches to take place over the weekend of Saturday, November 14.

Winning clubs will receive £3,750 from the competition’s prize fund with losing teams to receive £1,000.

If the ties are level after 90 minutes the result will be determined by a penalty shootout. There is no extra time or replays at this stage.

United have landed arguably the toughest draw possible at this stage, with teams from the National League yet to enter the competition.

Ryan Peters’ side won’t exactly relish a trip to the Gallagher Stadium, having lost 2-1 to Maidstone United in the league just a couple of weeks ago.

Maidenhead are currently 18th in the table and just three points above the drop zone after Saturday’s deflating 4-0 defeat at Ebbsfleet United.

We will face Maidstone United in the FA Trophy Second Round Proper on Saturday 14th November https://t.co/0k0YRXgww9

— Maidenhead United (@MUFCYorkRoad) October 26, 2026

Slough Town have been handed a kinder draw on paper, away to Southern League Central Division promotion hopefuls Didcot Town.

Didcot - one of the lowest ranked sides left in the competition - made it through to the second round with a 2-1 home win over Poole Town on Saturday.

They are currently second behind leaders Winslow United in the Central Division but play two levels below Slough Town who last week saw new investment come into the club through the Kuwait-based investment group, Development Holding Company (DH).

Slough – currently six points from safety at the bottom of the National League South - appointed Steve McKimm as first team manager last week with Barry Moore and Mark Watson also joining his coaching team.