The 19-year-old signed a new long-term contract at Stamford Bridge in July, committing his future to Chelsea until 2032, before moving to Portugal for the 2026-27 season in search of regular senior football.
Sporting appeared to offer an attractive environment for the winger's development, given the club's reputation for bringing through young talent. However, Derry has found opportunities limited during the opening months of his loan.
At the time of the latest report, his only start had come in the Allianz Cup against Marítimo, where he played 73 minutes. He was subsequently an unused substitute against Casa Pia and Shakhtar Donetsk, the latter fixture taking place at Stamford Bridge.
That return to west London could have offered a reminder of home for the Cobham graduate, but he watched from the bench as Sporting secured a 1-0 victory over the Ukrainian side.
The Portuguese club have also undergone a change in the dugout. Rui Borges has departed, with Paulo Fonseca appointed as his successor after leaving Lyon. Derry will now hope to make a positive impression on the new manager and improve his chances of regular involvement.
Chelsea will be monitoring the situation closely, with the intention that the teenager returns to Cobham next summer having gained valuable experience abroad.
Derry had made three senior appearances for Chelsea before leaving on loan. Liam Rosenior handed him his debut as a late substitute in the FA Cup victory over Hull City, and he also featured in the subsequent cup win against Wrexham. Interim head coach Calum McFarlane later gave him his Premier League debut in May.
That appearance ended painfully when Derry suffered a head injury following a collision and was stretchered off before being taken to hospital. The injury was not serious, and he returned to the Chelsea bench a couple of weeks later.
His new contract in July reflected the club's confidence in his potential. Derry described the agreement as a dream come true and spoke of his ambition to become part of Chelsea's future.
“It's a dream come true, obviously, to commit my future to such a big club like Chelsea,” he said.
“After having a little sniff of playing for the first team I couldn't have thought of anywhere else I'd rather be for my future. So it was a no-brainer.”
For now, the priority is finding a route into Sporting's team. A new manager gives Derry an opportunity to make his case again, but he will need minutes on the pitch if the loan is to deliver the development Chelsea envisaged.