And Pompey’s new arrival is out to man the supply lines to ensure the Fratton favourite is among the goals again next season. It’s a case of friends reunited as Holmes-Dennis settles in at his new club after agreeing a season-long loan from Huddersfield.
The 21-year-old is pals with Chaplin with the pair having the same agent.
That’s on top of knowing the likes of Drew Talbot, Curtis Main and Danny Rose from previous loan stints at Plymouth, Oldham and Oxford.
Holmes-Dennis will operate down the left flank for Kenny Jackett’s men next season.
Although primarily a defender, the former Charlton man has been recruited with his attacking instincts in mind.
He explained he’s looking to showcase the energy he feels he brings to the table – and help ensure the goals continue to flow for Chaplin.
Holmes-Dennis said: ‘I like to get up and down.
‘First and foremost I’m a defender but I like to attack.
‘Hopefully, I can show what I’ve got in that position.
‘After last season, I can see the lads are a tight-knit bunch.
‘I was just want to fit in and work as hard as I can to progress the club more.
‘I know a few of the lads here already.
‘Danny Rose, Curtis Main, Drew Talbot and Conor Chaplin.
‘I know Conor because we’ve got the same agent.
‘I’ve been with out with him a few times.
‘It’s encouraging there’s quality here and they are a good, welcoming bunch of lads.
‘It should make it easier to settle in for me.
‘Hopefully, I can create some chances for the likes of Conor to score. That’d be good.
‘Defending is the main thing, obviously.
‘But with the way the game is progressing it’s good to have an attacker in the form of a wing-back or left-back.
‘At Huddersfield the full-backs were up and down and creating a lot.
‘Hopefully we can do the same here.’
Holmes-Dennis could have been calling himself a Premier League player this season after his parent club’s promotion last term.
He got on the pitch in both legs of their semi-final win over Sheffield Wednesday before the Terriers defeated Reading at Wembley.
After 15 appearances in his first season following a move from Charlton, it’s minutes on the pitch which count for the player.
That’s why the switch to Pompey appealed in front of other options in the Championship and League One.
Holmes-Dennis said: ‘This is such a big club and they should be higher.
‘I always followed Portsmouth from when I was younger and they were in the Premier League and Championship.
‘It’s a massive club and is run professionally.
‘Game time is what I need and being around a good bunch of players.
‘So dropping down didn’t bother me too much.’