In the transfer market, young players like Marchena and Fernando Meira were brought in, and mixed with the experience of 31 year-old, Pierre van Hooijdonk, who arrived to replace Nuno Gomes, were meant to improve the team competitiveness.
However, the biggest event of the pre-season was the release of João Pinto, the longest-serving player on the club, and the incumbent captain.
Even the successful partnership of Pierre van Hooijdonk and João Tomás, with 36 goals between them, did not prevent the club from finishing in sixth place, 23 points behind winner Boavista.
His choices caused immediate controversy, the biggest being the release of Benfica veteran João Pinto.
José Manuel Delgado of Record predicted a difficult season for the German manager: "...he will have less tolerance from the fans than that offered to Artur Jorge (three match days), or Manuel José (four match days)..."[4] He forwent internationals like Paulo Bento[5] and Amaral,[6] but indulged on Marchena, Meira and Van Hooijdonk.
[7][8] All of this spending happened in spite of club-wide financial difficulties, from missed salaries for Michael Thomas,[9] to the basketball section of the club going months without pay.
It included a match celebrating the 50th anniversary of Olympique Lyon, and the Carlsberg Belfast Challenge against Linfield and Liverpool.
[12][13] Benfica started their 2000–01 Primeira Liga campaign on the road in a Clássico match against FC Porto, on 19 August 2000.
[14] João Marcelino stated that Porto "...had some luck in the way they obtained their first goal (shot from Alenichev deflected off Calado and betrayed Enke)...", allowing them to manage the lead until the end.
[18] Benfica won their second home game of the season, on 18 September, against Estrela da Amadora, thanks to two goals scored by Van Hooijdonk in consecutive minutes near the end of regulation time.
[27] On 15 October, Benfica won its third league game of the season by defeating Belenenses one–nil behind Marchena's goal.
[29] Benfica played their last game of the month against Campomaiorense on the 29th, winning with a double from João Tomás, scored within a space of ten minutes from each other.
Van Hooijdonk and João Tomás scored a goal each, within a 4-minute interval just before the final whistle, to give their team the three points.
[38] Following the win, Mourinho requested a contract extension as a demonstration of faith in the work he had put in along with his assistant: "Me [Mourinho] and Mozer thought that the only way to end speculation and the constant threat of being sacked in the event of a bad result...was renewing our contracts for another season.
They parted ways with the club through an announcement in a press conference: "He [President Vilarinho] thought it was better not to accept our request.
We understood that decision showed a lack of trust in our work, and that we should offer our resignation..."[39] Benfica immediately appointed Toni – a long-time favourite of the President – as the new manager.
Later, Milinkovic put the Ribatejo side in the lead, resulting in the fourth loss in seven matches in away games for Benfica.
[43] In the last match of the year 2000, Benfica met a struggling Gil Vicente, who were at the bottom of the Primeira Liga standings.
[37] Unable to unlock the 0–0 draw, the club suffered their eighth winless league game of the season.
[44] Early in January, Benfica played away from home, at Louletano, in a fifth round match of the Taça de Portugal.
[35] Manuel Queiroz wrote: "...A thrashing that did not transpire what really happened in the field, because Fernando Santos' team – in the best performance of the season – completely demolished a Benfica that never entered the game..."[51] Benfica's last game of the month was played on the road on the 29th, against the Aveiro side, Beira-Mar.
Roger and Van Hooijdonk increased their lead by two goals, until Nuno Valente settled the final score.
[52] Benfica had an opportunity to take the top place in the league table with a victory in that game, but they were unsuccessful at breaking the 0–0 draw.
[61] The game ended in a 3–0 defeat – their tenth loss within the league, matching their previous record in the 1996–97 season.
A final score of 1–1 saved Benfica from a record fourth straight loss, and gave the Porto-based side their first point all season against a top 7 team.
"[71] Benfica finished in a record-breaking sixth place after the 34-game season with a tally of 15 wins, 9 draws and 10 losses that, together, summed up to 54 points.
Note 2: Players with squad numbers marked ‡ joined the club during the 2000–01 season via transfer, with more details in the following section.