Mo Eisa is on Pompey’s radar as they draw up contingency plans.
Coventry are in pole position to land Conor Chaplin, with Bristol Rovers and Barnsley also declaring an interest in the striker.
The Blues are willing to sell Chaplin should an offer meet their valuation.
However, Kenny Jackett is prepared to reject low bids in favour of retaining the 21-year-old, despite the forward’s ongoing desire for regular first-team football.
Certainly, Pompey are in a strong bargaining position considering the interest demonstrated by fellow League One clubs.
In the meantime, Cheltenham’s Eisa is on the shortlist of forwards eyed as potential Chaplin replacements.
Should their academy graduate depart, the Blues intend putting money received from the sale towards recruiting another striker.
A sizeable Chaplin fee will undoubtedly bolster Jackett’s strength within the transfer market.
Among those being considered is the prolific Eisa - a player linked with Fratton Park since the end of last season.
The highly-regarded striker struck 25 goals for Cheltenham last season as they finished 17th in the League Two table.
Earlier this year, then Robins chairman Paul Baker slapped a £1.5m price tag on their prized asset, while in the past week the club have turned down an approach from Peterborough.
Yet the 23-year-old continues to be courted by a number of clubs as Cheltenham seek to hold out for bigger offers.
Recruited from Greenwich Borough in the summer of 2017, Eisa went on to enjoy an outstanding maiden Football League season.
Regardless of how Pompey’s interest in Eisa develops, Jackett is well aware he requires a replacement should Chaplin clinch a move.
The Blues hope to secure at least two more players during the transfer window – on top of filling the hole left by Chaplin’s potential exit.
Anton Walkes will complete his long-awaiting permanent Fratton Park switch once no longer required by Spurs during pre-season.
The Premier League club have nine players still present at the World Cup, ensuring domestic numbers are down following Monday’s training return.
Jackett also hopes to capture attacking midfielder Sean Longstaff from Newcastle on loan.
The Magpies returned for pre-season training on Friday – and today head to Ireland for a training camp.
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