1999–2000 S.L. Benfica season

After sacking Scottish coach Graeme Souness, Benfica appointed UEFA Champions League-winning manager Jupp Heynckes.

Tote arrived to replace Rushfeldt, who signed and practised with the team, before being recalled back by Rosenborg with disagreements over his transfer.

Benfica started their campaign with a six-game winning streak in their first seven league games, topping the league until December; when a record-setting loss to Celta de Vigo, the greatest in its history, negatively affected the team mentality, causing them to drop to third place in Matchday 19, which would become their final position, finishing eight points behind Sporting, but securing a position in the upcoming season's UEFA Cup.

Their first game in Lisbon was against Bayern Munich on 10 August, and four days later they participated in the Trofeo Memorial Nereo Rocco against AC Milan.

[15] The Argentine had appearances on his national team and was the first choice at Estudiantes, while the German had its breakthrough at Borussia Mönchengladbach only a few months earlier.

[22] On 12 September Benfica visited Azores and beat Santa Clara 3–0 to move to top of the league table, tied with five other teams.

Benfica lost their first league match; with a display that Record characterized as being under a Halloween spell; that resulted in "their worst performance of the season, and seeing Porto close in on the top of the table.

[35] After a one-week break for the Taça de Portugal,[36] Benfica visited Estádio das Antas for the Clássico against Porto.

[39][40] At their next training session hundreds of fans booed the team, and the club president compelled his players to apologize for their performance.

"[45] In the second leg of the UEFA Cup against Celta de Vigo, the Spaniards and Heynckes fielded lineups almost entirely composed of reserves and the match ended in a one-all draw.

[56] Chano was decisive in unlocking the game in the perspective of Record: "He was the vitamin that gave imagination and clarity to Benfica's midfield".

[57] They won a fourth consecutive time, beating Vitória de Setúbal in Estádio do Bonfim and gaining ground on Porto and Sporting (both of whom lost points).

[58] On 22 February, Benfica hosted Farense knowing that a win would put them one point behind the joint Primeira Liga leaders.

José Manuel Delgado wrote in his match report for Record: "Heynckes' defence show[ed] inexplicable passivity, and Quinzinho was a loose threat that no one could stop.

[59] For their last February match, Benfica visited Estádio José Gomes to face the local team, Estrela da Amadora.

[56] Two goals by Gáucho and another by Kenedy gave them their first league loss since 19 December, with Porto and Sporting regaining a four-point lead.

[64] Although the team led the game early, another late goal and the subsequent loss allowed both rivals to increase their lead.

[65] On 1 April Benfica faced Porto in the second Clássico of the season, and a second-half goal by Sabry helped the club defeat their historic rivals.

[66] An early dismissal of José Soares helped them win easily, with Sabry scoring in a fourth consecutive game.

[69] A week later the team lost their second straight match (their seventh defeat of the season) to União de Leiria 2–1, despite scoring first.

[70] On 30 April Benfica returned to top form, and in Miguel Costa Nunes opinion, defeated a "debilitated and riddled with internal conflicts" Vitória de Guimarães 3–0.

[71] In the penultimate game of the season, Benfica faced Sporting for the third time; in their previous meetings, the club had tied once and lost once.

[75][76][77][78] Win Draw Loss Postponed The squad for the season consisted of the players listed in the tables below, as well as staff member Heynckes (manager).