The match against The Boro will be Danny Cowley’s first taste of the FA Cup responsible for the Blues, and the former Huddersfield Town boss and the club both have a high history in the competition.
Harrow progressed into the first round with a 4-2 victory over Chelmsford City, and will make the trip to Fratton Park next month.
In 2017,Cowley guided, then non-league, Lincoln City to the quarter-finals of the competition and picked up a few scalps along the way. After knocking out Ipswich Town, the Imps repeated the feat when Blues ever-present Sean Raggett netted an 89th minute winner against Premier League Burnley at Turf Moor. However, the dream came to an end as Cowley’s side suffered a 5-0 defeat against Arsenal.
The Blues are, of course, two time winners of the historic trophy and three times runners up, but have had varying success in the competition over recent years.
Last season, Pompey reached the third round but fell to a thin defeat to Bristol City and were deleted by Arsenal in the fifth round the season before.
The club’s most recent scalp came in 2019 when Andre Green fired home an injury time winner against Norwich City at Carrow Road.
The first round ties are set to be played across November 5 to November 8.
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