The 2008–09 European football season was Sport Lisboa e Benfica's 105th season and their 75th consecutive season in the top flight of Portuguese football. The season ran from 1 July 2008 to 30 June 2009, with Benfica competing domestically in the Primeira Liga, Taça de Portugal and Taça da Liga. The club also participated in the UEFA Cup, since they finished fourth in the Primeira Liga the previous season.
After José Antonio Camacho's March 2008 resignation, Benfica did not have a permanent manager. The club inquired about Quique Sánchez Flores, Sven-Göran Eriksson and others, ultimately choosing Flores. Rui Costa led the transfer activity as Benfica continued to invest heavily, spending nearly €19 million on Javier Balboa, Carlos Martins, Pablo Aimar and Sidnei and bringing in José Antonio Reyes and David Suazo on loan. Major departures included Rui Costa, Cristian Rodríguez, Petit and Nélson.
Benfica's season began inauspiciously, but they quickly recovered, gaining momentum domestically and eliminating Napoli to qualify for the group stage of the UEFA Cup. Until January, the club's performance fluctuated in their European campaign and the domestic league. Although they finished last in the former, they reached first place in the Primeira Liga for the first time since 2005.
In the new year, Benfica suffered their first league loss, falling to second place and beginning their erratic spell. Despite a sterling League Cup (where they earned their first honour in four seasons), the club's league play was not as impressive. They battled Porto for first place until March, when they had another costly loss and were passed by Sporting CP. Benfica tried to retake second place in the remaining eight matches, but in early May, the club dropped five points, sealing their fate; they finished third, missing the UEFA Champions League for a second consecutive season.
Season summary
Pre-season In February 2008, club president Luís Filipe Vieira announced that a new director of football for 2008–09 had been selected. Although he did not name the individual, one month later Rui Costa confirmed that he would oversee Benfica's football division. With the unexpected resignation of head coach José Antonio Camacho on 10 March, assistant Fernando Chalana led the team through the final two months of the season. On 12 April Spanish manager Quique Sánchez Flores confirmed contacts from Benfica, who wanted him to take over the team immediately. Sánchez Flores declined the offer because he did not wish to be a temporary manager, and preferred to join a team at the beginning of the season.
On 7 May, Vieira and Rui Costa travelled to Manchester to persuade Sven-Göran Eriksson to return for a third stint with Benfica. Although both sides confirmed the meeting, after more than a week without an agreement the club moved on to other coaching candidates. Benfica then contacted Getafe manager Michael Laudrup and Brazilian manager Zico. After failing to come to terms with either, the club turned to first choice Sánchez Flores and signed him on 24 May. Sánchez Flores would be aided by technical assistant Fran Escribá, goalkeeper coach Emilio Álvarez and fitness coach Pako Ayestarán, with Diamantino Miranda and Chalana links to club management.
Benfica made their first transfer deals in late April, adding Ruben Amorim and Jorge Ribeiro, both of whom had previously played for Benfica. With Sánchez Flores in charge, Benfica added midfielder Hassan Yebda on a free transfer and spent €4 million on Javier Balboa from Real Madrid. Balboa was signed only three days after the shock transfer of former Paris Saint-Germain loan Cristian Rodríguez to rival Porto. Although Benfica negotiated with PSG and the Uruguayan for months, the sides could not reach an agreement. During the next few weeks Benfica continued to spend, paying €3 million to Recreativo de Huelva for Carlos Martins and €6.5 million two weeks later, after a prolonged transfer saga, to Real Zaragoza for Pablo Aimar.
The club's pre-season began on 8 July with two days of medical tests. Benfica's first training session was held two days later, nine days before their first pre-season match with Estoril. After a draw with Estori, the club lost Guadiana Trophy matches to Blackburn Rovers and Sporting CP. That week Benfica made more squad adjustments, paying €5 million for 18-year old Sidnei and releasing Petit after six years with the club. Early in August, Benfica won the Cidade de Guimarães Trophy against Paris Saint-Germain and Vitória de Guimarães, drawing with the former and defeating the latter. Before their presentation match with Feyenoord, Benfica signed Spanish winger José Antonio Reyes in a €2.6 million loan deal. In the match with Feyenoord, Óscar Cardozo scored the winning goal for Benfica. The club ended its preparation for the season against Inter Milan on 15 August in the new Eusébio Cup. After a goalless draw in regular time, the Milanese won on penalties.
August–September Benfica's first competitive game was an away Primeira Liga opener against Rio Ave. Sánchez Flores did not have Reyes, and Jonathan Urretaviscaya started instead. At the Estádio dos Arcos, the home team scored first with a 55th-minute goal from José Semedo. A minute later Benfica evened the score, with Urreta assisting Nuno Gomes for the 1–1 final result. It was the fourth consecutive time that Benfica failed to win their league start. Sánchez Flores said that Rio Ave created unexpected problems: "It was not a easy game. We had a quality opponent, who left us trailing when we were not expecting it." During the last week of August Benfica brought in Honduran striker David Suazo on loan, sold right-back Nélson Marcos to Betis and was paired with Italian side Napoli in the UEFA Cup first-round draw on 29 August. A day later, Benfica hosted Porto for the first Clássico of the season. The visitors started better, converting a 10th-minute penalty kick for a Kostas Katsouranis foul against Lucho González. In the 56th minute, Cardozo exploited a mistake by Helton to head in the equaliser. Three minutes later Katsouranis was sent off, but Benfica held the tie until the final whistle. Quique Flores said, "It was a good game. In normal conditions we would have done better, but circumstances made it a little harder."
After the first two weeks of September were dedicated to international football, Benfica returned to competition on the 18th. In the first leg of the qualifying stage for the UEFA Cup, the club faced Napoli at the Stadio San Paolo. Suazo began the scoring for Benfica with a 16th-minute header, but the lead lasted only two minutes. Luigi Vitale tied the score, and Germán Denis scored again for Napoli a minute later. In the second half Christian Maggio added another for Napoli, with Luisão scoring for Benfica three minutes later. Although Quique Flores believed that the loss was a combination of referee mistakes and errors by his players, he believed his club could qualify. The following Monday, Benfica visited the Estádio da Mata Real to play Paços de Ferreira in a 4–3 win. Nuno Gomes scored the one-nil in the sixth minute, and Paços equalised less than 10 minutes later. Before half-time, Quique's men added two more goals. In the restart, Paços made the match 3–2 in the 63rd minute before Benfica responded with a fourth goal from Jorge Ribeiro. Before the final whistle, William scored another for Paços. Sánchez Flores said about his first win at Benfica, "I am happy for the fans, who needed this to feel that their team also fights for the league." On 27 September, Benfica hosted Sporting CP for the first Lisbon derby of the season. With the visitors enjoying a four-point lead in the league, Benfica had to win to move up in the standings. The game's only goals were in the second half, the first in the 67th minute when Pablo Aimar assisted Reyes; four minutes later, Sidnei headed in a free kick from Carlos Martins for the second. Sánchez Flores was encouraged by the victory against a team as strong as Sporting.
October–November October began with a crucial match against Napoli. Benfica had only defeated Italian teams four times, most recently on 29 March 1994. The club won with two second-half goals (an opener from Reyes and a confirmation goal from Nuno Gomes), qualifying for the group stage. The victory placed Sánchez Flores in club history, since Benfica had never eliminated an Italian team after losing the first leg. The game was Benfica TV's first broadcast. On 6 October, the club played Leixões on the road. With the top of the Primeira Liga just three points away, Benfica could not beat the home team, losing two points; they led the game for over an hour, but were stopped by an 88th-minute equaliser from Wesley. To Sánchez Flores, the draw was due to Benfica's performance: low possession, missed passes and fouls resulting in free kicks. The following day, Benfica heard from UEFA headquarters in Nyon that their UEFA Cup group would include Olympiacos, Galatasaray, Hertha BSC and Metalist Kharkiv. After a two-week break for international matches, competition resumed with the Taça de Portugal on the 18th. Benfica met third-tier side Penafiel at home; unable to defeat them in regular and extra time, they required penalty kicks. Luís Dias missed one for Penafiel, enabling Benfica to advance to the fifth round. Sánchez Flores said, "We wanted to play good football, but that did not happen." The following Thursday, Benfica travelled to Berlin to play Hertha in the Group B opening game. They took the lead with a 51st-minute goal from Ángel Di María, but Hertha responded with a 74th-minute equaliser when a shot by Marko Pantelić was deflected by Maxi Pereira. Captain Nuno Gomes said that although an away draw in Europe was a good result, Hertha's equaliser was bitter for the team. October ended with a home game against Naval. After a first half in which both teams failed to convert opportunities, Benfica scored their opening goal in the 71st minute. Naval evened the score eleven minutes later, but Cardozo responded with an 86th-minute winner for Benfica. Sánchez Flores said that the game was difficult because of his club's inconsistency.