The two situations sit at opposite ends of the same process, as Xabi Alonso's new-look squad takes shape ahead of the 1 September deadline, with Chelsea currently carrying 39 senior professionals on their books.
Nottingham Forest are working on a deal to sign Delap, who has been made available for sale at £50million and is currently training away from Chelsea's first-team squad.
It remains unclear whether any deal would be structured as a permanent transfer or a loan, though the two clubs are known to have a positive working relationship following previous dealings. Delap was left out of Chelsea's squad entirely for Monday's Premier League opener against Fulham, having already lost the number nine shirt to fellow forward João Pedro the previous week.
His potential departure comes just over a year after his £30million arrival from Ipswich Town, a move that has failed to deliver the desired impact: shoulder and hamstring injuries restricted him to a single league goal last season. Should he join Forest, Delap would provide competition for Chris Wood and Igor Jesus at the City Ground, continuing a summer in which the club have already added defender Ousmane Diomande from Sporting for £34million, alongside free signings Xaver Schlager and Steve Benda.
Forest have also raised significant funds through outgoing deals, selling England midfielder Elliot Anderson to Manchester City for a club-record £116million and striker Taiwo Awoniyi to Coventry City for £9million.
Chelsea's stance on Jamie Bynoe-Gittens tells a rather different story.
According to Corriere dello Sport, AS Roma tried to tempt Chelsea with a loan proposal worth around £2.6million upfront, plus a potential permanent fee of roughly £34.5million, but the Blues rejected the offer outright and are demanding an obligation to buy rather than an option, along with improved financial terms overall for a player they signed from Borussia Dortmund for £52million last summer.
Gittens endured a difficult second half of last season after a hamstring injury ruled him out for the final four months of the campaign, having already struggled to establish himself before that setback with just a single goal in 27 appearances.
"It was hard, because this was the first muscle injury I've had. I've never had hamstring injuries before," Gittens said.
"It was a challenge at the start, but I'm better now so I feel more confident. I'm feeling much better, more confident now my body is better, the hamstrings are good, so I'm just waiting for the season to start."
Opportunities could remain hard to come by regardless, with Chelsea having spent £117million on Morgan Rogers from Aston Villa and a host of attacking options including Cole Palmer, Estêvão, Pedro Neto, Valentín Barco and Geovany Quenda all competing for the same forward positions.
A loan elsewhere may still make sense before deadline day, but for now, Chelsea have made clear they are not simply prepared to let Gittens leave on the cheap. The winger himself insisted last month that he wants to make his move to Stamford Bridge work.