But now it appears Everton are ready to try and secure the former England international for the longer-term.
Calvert-Lewin had a strange and wildly inconsistent season in 2023-24, scoring in total seven goals by the end of the campaign.
But those bald statistics don't explain the complexity of his season, which mirrored the Blues' own travails in what was the most challenging and controversy-filled campaign any club experienced in Premier League history.
After netting the winner at West Ham on 29th October, Calvert-Lewin then went on a goal-drought that meant he failed to score again until Everton travelled to Newcastle United at the beginning of April.
During much of this time the Toffees were struggling to recover from two points deductions for PSR breaches while waiting for news as to whether 777 Partners would be allowed to complete their takeover from Farhad Moshiri.
From the 16th December until the next match after that Newcastle game - when Calvert-Lewin finally broke his duck - Everton didn't win a single match in the Premier League.
It looked very likely that the club would finally fall through that relegation trap door which they had only managed to avoid by the slimmest of margins in the two previous campaigns.
While the 27-year-old centre-forward was having such a difficult time, manager Sean Dyche did eventually turn to his other options, most of all summer 2023 signing Beto.
But the Portuguese striker struggled badly to adjust to and perform effectively in, the Premier League managing only two goals all season long.
So, when the season ended Everton would be faced with a choice: offer Calvert-Lewin a new deal or consider cashing in on their centre-forward before he left for free next year.
Now it is up to the player himself as to whether he will opt to sign that new contract or seek his future elsewhere.
Everton will have to sell this summer, both to help stabalise their precarious finances and to fund any signings to improve a small and obviously weak squad.