One-time Portsmouth forgotten man bidding for Football League return - but there's an ex-Blues and Ipswich boss standing in his way

Although former Pompey boss Paul Cook is currently barring the way.

Louis Dennis’ time on the south coast was largely unremarkable, with eight appearances during the 2018-19 campaign.

Indeed, a good reputation among supporters was largely based upon few having actually seen him play, leading to regular clamour for inclusion in Kenny Jackett’s team.

In truth, aside from the cross for Brett Pitman’s acrobatic strike against Oxford United and a Checkatrade Trophy finish at Southend, Dennis made little impact in 13 months with the Blues.

At one time declared as the answer to Pompey’s number 10 hunt, by boss Jackett himself, he was sold to Leyton Orient in August 2019.

It represented a small profit on a player recruited from Bromley the previous summer on a free transfer, arriving alongside Ronan Curtis, Craig MacGillivray, Lee Brown and Tom Naylor.

Nowadays he’s back with the non-leaguers, following a disappointing two-year spell at Orient which yielded just 18 League Two starts.

He returned to the Ravens in August 2021 as a free agent – three years after his departure for Pompey – and subsequently enjoyed the regular first-team football denied him in the Football League.

Bromley’s finishing position of seventh in the National League this term saw them face Woking in the play-offs on Wednesday evening.

Dennis started the match, featuring for 48 minutes, before replaced by Adam Marriott, as they claimed a 2-1 victory to reach the semi-finals.

Andy Woodman’s men now make the trip to Chesterfield on Sunday for the right to play either Notts County or Boreham Wood in the final – with a pace in League Two at stake.

Their opponents are managed by Cook, with the Spireites having claimed third spot in the National League with an excellent haul of 84 points, yet still nowhere near the runaway top two.

Wrexham were crowned champions with 111 points and 116 goals, while Notts County finished second (107 points), that’s 23 points more than Chesterfield.

Still, having lost in the play-offs to Solihull Moors last season, Cook will be striving to ensure they fare better when hosting Bromley and Dennis on Sunday (3.30pm).

The former Blues boss will be joined in Chesterfield’s dug-out by a member of his League Two title-winning team – Gary Roberts.

Roberts, who totalled 20 goals in 80 appearances during his time at Fratton Park, is first-team coach with the Spireites.