The Arsenal U18s side will play Hertford Town U18s in the third round of the FA Youth Cup.
The clash is set to take place at 7pm on Tuesday, December 3 and will be held at Hertingfordbury Park, home of Hertford Town.
Hertford have now beaten two EFL sides, Cambridge United and Bristol Rovers, during their FA Youth Cup run.
While the young guns are entering the competition in the third round, after Hertford reached this stage with an excellent 4-3 victory over Rovers on Tuesday.
Hertford Town said the match: "Marks a huge day for not only the club, but for the Town of Hertford."
Under Jack Wilshere the then U19s reached the final of this competition back in the 2022-23 season, with a number of players who have since progressed to the under-21s and first team, including Ethan Nwaneri and Myles Lewis Skelly.
Tickets priced at £10 for adults, £5 and £1 concessions.