Delap completed a £30m transfer switch to Stamford Bridge in 2025, following Ipswich Town's relegation at the end of the 2024/25 Premier League season, where he scored 12 goals in his debut top-flight campaign at Portman Road.
However, he struggled to break into Enzo Maresca or Liam Rosenior's plans, with Joao Pedro the chosen focal point of Chelsea's attack under both managers.
The 21-year-old scored just one EPL goal across the full campaign and Chelsea are ready to let him go with Everton rumoured to be planning an offer.
Chelsea will want to recoup as much of the £30M they paid to land him from Ipswich last year and some reports claim they are pushing for a £40M fee.
Whatever happens in the weeks ahead, Hasselbaink believes he must move on, to stand a chance of reviving a promising career.
"He needs football. He can't have another season like he had at Chelsea,", he told WhoScored's The State of Play podcast.
"If that means he needs to go out on loan, he needs to do it, because he's too young to sit on the bench.
"He needs to kickstart his career again, score goals, and get that feeling back because every time he played for Chelsea, it felt a little bit like he was up against it.
"He needs to get the confidence of the manager that says, 'Don't worry with the first or second, just go and play'. I think he can be a top four club kind of striker, but he needs games."