The pair could both have well have moved to Fratton Park had Pompey met one player's price tag and the other’s wage demands.
But now Matty Godden and Freddie Ladapo are toasting promotion and preparing for a crack at the Championship next campaign.
The strikers' respective clubs Coventry and Rotherham have been promoted after League One clubs voted to curtail the 2019-20 season on Tuesday.
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How things could be different had the Blues signed either or both the players, though.
This time last year, Godden emerged as someone on Pompey’s radar – largely thanks to Peterborough chairman Darragh MacAnthony.
The Irishman revealed on Twitter the Posh had knocked back a bid from the Blues for the ex-Stevenage striker, who’d bagged 18 times in 2018-19.
Peterborough slapped a figure of £750,000 on Godden’s head, with Jackett confirming that was out of Pompey’s price range.
‘It was a verbal bid (for Godden), I phoned Darren Ferguson and discussed it with him, that was six weeks ago,’ Jacket told The News.
‘We haven’t put in another bid and, no, we are not going back for him. We discussed it and the price was too high.’
Godden would indeed leave London Road later in the summer – with an ex-Fratton favourite the catalyst for his switch.
Conor Chaplin departed Coventry for Barnsley, with Godden identified as his replacement.
And the former Scunthorpe man enjoyed a fine campaign for the Sky Blues, netting 15 goals in 33 games – including the winner a 1-0 win over Pompey in February – as Mark Robins’ men were crowned third-tier champions.
Unlike Godden, Pompey did meet Plymouth's they placed on Ladapo.
The ex-Cyrstal Palace ace had bagged 19 times the previous campaign when Argyle were relegated to League Two.
But wage demands were chiefly behind the breakdown of the potential transfer for Ladapo and Pompey turned their attention elsewhere.
Ladapo subsequently joined Rotherham for a club record in the region of £500,000.
He bagged 17 times in 39 appearances, with five of his efforts coming in the final seven games, to ensure the yo-yoing Millers finished second in the table to make an immediate return to the Championship.
In fairness to Pompey, the strikers they went on to sign haven't exactly been a disappointment.
The first marksman to arrive was long-time target, Ellis Harrison, for a fee of around £450,000 from Ipswich.
Harrison's selfless play and ability to stretch defences has made him popular among fans, while he's bagged 10 goals in 37 appearances.
John Marquis would then move to Fratton Park for a substantial fee from Doncaster in July.
When his arrival was announced, it was undoubtedly a statement of intent from Pompey, as the ex-Millwall man bagged 67 times in three seasons at the Keepmoat.
Marquis has netted 14 goals in 46 outings for Jackett's men this campaign.
You’d expect him to build on that tally next term, no matter what division Pompey are playing in.
Nevertheless, you can’t help but wonder how the season would have played out had Godden and/ or Ladapo donned the star and crescent.