Indeed, the Blues’ last visit to Vale Park was in April 2000 in the old English League Division One, now known as the Championship.
The last fixture saw Tony Pulis’ men fall to a 2-0 defeat, with names including Darren Moore, Steve Claridge and Shaun Derry all featuring in the loss.
Twenty-two years later and in much different circumstances, Danny Cowley’s men take on the Valiants in a bid to continue their impressive unbeaten start to the League One campaign.
We’ve taken a look at the Blues’ last starting XI who featured in the last trip to Vale Park more than 20 years ago.
Here’s who appeared that day...
1. Russell Hoult
The keeper arrived at Pompey in January 2000 on loan from Derby, before he made the switch permanent a week prior to the game at Vale Park. The stopper made 44 outings for the Blues before a £450,000 move to West Brom in January 2001. Six years later, Hoult was sacked by the Baggies after an indecent video appeared online while he was wearing a club shirt. He would go on to have spells with Stoke, Notts County and Hereford before retiring in 2012 and managing Thringstone Miners Welfare for a season. Photo: NationalWorld
2. Darren Moore
Moore spent nearly two-years at Fratton Park, amassing 66 outings for the Blues. Although the centre-back was a fan favourite at PO4, the former Jamaica international has since become one of Pompey’s toughest rivals. Now head coach at Sheffield Wednesday, the 48-year-old is battling his former side to promotion from League One, with the two sides going head to head for a place in the Championship. Photo: Michael Regan
3. Dave Waterman
The Northern Ireland youth international was one of two players sent off at Vale Park as he was given his marching orders after 43 minutes. The midfielder made 88 appearances for Pompey before joining Oxford United in 2002. In 2005, Waterman returned to the south coast where he set up the Oakley Waterman Caravan Foundation in honour of his late son Oakley. The charity enables children with life-threatening illnesses to have quality time with their families. He still runs the charity to this day. Photo: Gary M. Prior
4. Justin Edinburgh
The fan favourite made 38 appearances for Pompey after making a £175,000 move from Spurs in March 2000. After retiring in 2006, Edinburgh became boss at Billericay before spells at Newport, Gillingham, Northampton and Leyton Orient. Tragically, the former defender died in 2019 after guiding the O’s to National League glory, aged 49. Photo: NationalWorld