Should Benfica sign free agent winger Raheem Sterling

Benfica, who are looking to bolster their attacking options, could target free agent winger Raheem Sterling, who has emerged as a tantalizing signing. The 31-year-old Englishman, was recently released from Chelsea and would bring a wealth of experience to the club that could elevate the Benfica's Portuguese League and European campaigns.

Benfica's concern could be the rust that Sterling may have due to lack of action this season, as he has unfortunately seen zero game action, after being deemed surplus at Chelsea and trained away from the first team throughout the first half of this season.

What you can not do is take Sterling's pedigree away, the four time Premier League winner with Manchester City, boasts 123 top flight goals and 75 assists in 396 appearances career wide. Sterling would inject pace, dribbling flair and clinical finishing from either wing spot.

Sterling spent last season on loan at Arsenal where he appeared in 28 games of action across all competitions, scoring once while providing five helpers in 1,143 minutes of action.

Sterling is coming off a £325,000 weekly salary with Chelsea and would have to take a significant pay cut if there was any hope of him making the move to Benfica. It would be a low-risk move for both the club and the player who would be looking to re-ignite his career, while Benfica would count on a boost toward silverware.  

Benfica underwhelms during winter transfer window

Benfica fans have been left scratching their heads after the 2026 winter transfer window slammed shut. With the team struggling in the Portuguese League and hoping to prolong their European campaign, they desperately needed reinforcements to bolster the squad depth.

Yet, Benfica's activity was disappointingly underwhelming, which perhaps shows the teams financial caution and spending much more than they already have. 

On the incoming side, the Eagles managed just two notable acquisitions. The return of veteran attacker Rafa Silva from Besiktas on January 22 for around €5 million brings experience and flair back to their attack. While Amadora's Swiss army knife Sidny Lopes Cabral joined in early January for €6 million, adding depth to the current squad.

The club's out going moves were move of the trimming of the hedges then actual big splashes. David Jurasek departed on January 16 for €3 million, while center back Adrian Bajrami moved for €900K on January 1 to FC Luzern.

The club also loaned left back Rafa Obrador to Torino for the remainder of the season with an option to buy. This sparse business is a missed chance to address midfield woes and injury concerns. Will these very minor moves be enough to salvage the season? Time will tell.

Benfica and Real Madrid ready for rematch in playoff

Benfica and Real Madrid will face one another once again following a thrilling final game of the league phase in the Champions League after UEFA drew the two clubs together for the playoff stage of the competition.

Benfica are going into the head to head encounter on a high after securing a 4-2 victory over the Spanish giants at the Luz. The win snuck Benfica into the 24th and final playoff spot after a last play goal by keeper Trubin that has been watched around the globe.

Benfica will host the first leg of the playoff on February 17 before travelling to Madrid and facing Real at the Bernabeu on February 25. Benfica are hoping that lady luck will be on their side once again.