The 1995–96 season was Sport Lisboa e Benfica's 92nd season in existence and the club's 62nd consecutive season in the top flight of Portuguese football, covering the period from 1 July 1995 to 30 June 1996. It involved Benfica competing in the Primeira Divisão and the Taça de Portugal. Benfica qualified for the UEFA Cup by coming third in previous League.

After failing to renew the title in the past season, the club brought in several players during the transfer market, with Ricardo Gomes, Valdo, Calado and Marcelo assuming regular starter roles. However, the club lost all of his more historic players as the case of Neno, Vítor Paneira, Isaías and César Brito. With the animosity around Artur Jorge increasing, poor results in September caused his departure. Despite an irregular season in the league, various winning streaks helped the team reach their second-place finish by 23 March, after a home win against Porto. In the Portuguese Cup, a strong performance from Marcelo throughout the competition, who finish as the tournament top scorer, guided the team to the final, where João Pinto delivered the trophy after scoring a double.

The second season of Artur Jorge started with much more distrust over his abilities. From the large number of signings in the year before, only a handful prove noteworthy, and Tavares and Nelo even showed a complete inability to play for a big club. Despite that, more exits followed, with a 28-year-old Vítor Paneira, and the club league topscorer in the year before; Isaías, causing the most anger. Benfica signed mostly in Portugal, as with the league top goalscorer, Hassan, but also searched in Europe, bringing Valdo and Ricardo Gomes, back from France.

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