Today’s encounter with Charlton could feature two former News/Sports Mail Pompey players of the season, with Jason Pearce and Ricky Holmes likely to line-up for the hosts.
Former Blues player Jason Pearce was the 2011/12 player of the year, while Ricky Holmes scooped the prize two years later after the 2013-14 campaign.
Both players soon left the club following their impressive season’s at Fratton Park.
We look back on their time in a Pompey shirt.
Centre-half Pearce began his career with Pompey and signed his first professional deal in the summer of 2006 with Harry Redknapp at the helm.
However, he failed to make a first-team appearance before joining Bournemouth.
There he established himself, before Steve Cotterill brought him back to Fratton Park for the 2011-12 season for an undisclosed fee.
Pearce made his debut on August 11, 2011, against Reading, finally representing the club that gave him his first professional contract five years prior.
The defender’s impact was immediate, helping the Blues secure a clean sheet, and inspiring the financially-troubled team to a 1-0 victory.
Pearce’s first goal came 12 games into the season, when he headed in a consolation goal for managerless Pompey in a 3-1 defeat to Derby.
His second goal came in better circumstances, scoring in the 3-0 victory over Peterborough on January 28, 2012.
Despite the club’s struggles on and off the pitch, there was a silver lining for Pearce, who was announced as Pompey’s captain for the remainder of the season in March 2012.
The central defender’s success on a personal level continued when he won seven out of a possible nine end-of-season awards following the clubs relegation from the Championship in 2011-12.
Pearce made 44 appearances for the Blues.
In May 2012, Pearce was sold to Leeds for an undisclosed fee.
He went on to make 99 appearances at Elland Road, before a switch to Wigan in 2015.
After one season with the Latics, he was once again on the move to join Charlton for an undisclosed fee.
Ricky Holmes will be remembered best for his successful 2013-14 season with Pompey.
He shook off all competition, including top-scorer Jed Wallace, to win the News/Sports Mail Player of the Season.
Then manager Guy Whittingham signed Holmes to a two-year deal in June 2013, after the expiry of his contract at Barnet.
He scored twice for the Blues as he attempted to help the club rebuild in League Two.
Holmes won over the Fratton faithful with his performances, and scored his first goal on September 14 in a 2-1 victory away to Burton Albion.
His first goal was a memorable one, rebounding home from on-loan Sunderland stopper Jordan Pickford’s save.
The winger’s second of the season was fortunate but equally important as it came in a 3-2 home victory against Exeter.
Holmes claimed the first goal of the game as his intended cross found it’s way past the keeper.
The wide man earned himself the reputation of a great crosser, and recorded assists regularly throughout the season.
The Essex-born winger’s form continued into May, and he twice set-up hat-trick-hero Danny Hollands on the final day of the season.
The two assists in the 3-3 draw against Plymouth took his league tally to nine assists.
Holmes was unable to replicate this form in the following season, and signed permanently with Northampton after a January loan spell.
He finished his Blues career with 53 appearances.
After 18 months with Northampton he handed in a transfer request and was snapped up by Charlton in June 2016.
He has so far played 53 games and scored 19 goals for the Addicks.