It’ll be the Blues’ first encounter against the phoenix side after the original Hereford United were wound up in 2014.
However, there have been 11 contests between the two teams, with Pompey claiming victory in seven of the meetings.
Their most recent encounter came in 2009 when Paul Hart’s Premier League men welcomed the League Two side in the second round of the League Cup.
Goals from Freddy Piquionne, John Utaka, Niko Kranjcar and Richard Hughes sealed the 4-1 victory at Fratton Park.
But which players were in the starting XI that evening – and where are they now?
We’ve taken a look at the last Pompey side to take on Hereford ahead of their upcoming FA Cup clash in November.
. PORTSMOUTH, ENGLAND - AUGUST 25: Younes Kaboul of Portsmouth is challenged by Craig Jones of Hereford United during the Carling Cup second round match between Portsmouth and Hereford at Fratton Park on August 25, 2009 in Portsmouth, England. (Photo by Bryn Lennon/Getty Images)
Pompey were drawn against Hereford in the first round of the FA Cup on Monday. Photo: Bryn Lennon
. Asmir Begovic
David James’ back-up keeper got his chance in the League Cup, which was one of his 18 appearances between the sticks for the Blues. The 35-year-old is still going strong at Everton, playing second-fiddle to Jordan Pickford at Goodison Park. The keeper has made two outings this term, one of which came in a 1-0 win over West Ham in the Premier League. Photo: Phil Cole
1. Asmir Begovic
David James’ back-up keeper got his chance in the League Cup, which was one of his 18 appearances between the sticks for the Blues. The 35-year-old is still going strong at Everton, playing second-fiddle to Jordan Pickford at Goodison Park. The keeper has made two outings this term, one of which came in a 1-0 win over West Ham in the Premier League. Photo: Phil Cole
2. Nadir Belhadj
The former Algerian international was a regular at left–back during his two-year stay at Fratton Park, where he amassed 65 outings as well as scoring seven goals. Despite being 40-years-old, the left-back is still playing football in the middle-east for Qatari side Muaither SC. Belhadj has featured just once this season, coming in the Amir Cup after moving to the side in January. Photo: Bryn Lennon
3. Younes Kaboul
The French centre-back moved to Fratton Park in 2008, joining the Blues in a £6.6m switch from Spurs. The defender went onto feature 50 times for Pompey over two seasons, before returning to White Hart Lane in 2010. After spells at Sunderland and Watford, the defender hung up his boots in 2018 and now runs a care home for people with mental disabilities in Belgium. Photo: Bryn Lennon
4. Anthony Vanden Borre
The centre-back is mostly remembered for his red card against Blackburn in 2010, causing the famous ‘I don’t know Jeff’ line from Chris Kamara. It was one of 25 outings he made for the Blues during a season-long loan stay from Genoa. After breaking his contract with Anderlecht in 2021, the former defender opted to venture out to Dubai where he set up his own youth academy. Photo: Christopher Lee