october began with a home match against vitória de guimarães. miccoli opened the scoring for benfica in the 20th minute, but tiago targino equalized a few minutes later. simão put benfica back in front with a deflected shot that beat márcio paiva, ensuring a third consecutive win that reduced the distance to the league leader to four points. after another interruption for international football, benfica returned to competition with a clássico against porto. despite porto being the favourite to win, benfica won 2–0 with two goals from nuno gomes. it was benfica's first away win at porto since 1990–91, when césar brito also scored a double. on the following thursday, benfica visited el madrigal to play villarreal. on the half-hour mark, benfica lost their goalkeeper quim to injury and replaced him with the 19-year-old rui nereu. in the second half, villarreal scored from the penalty spot. five minutes later, manuel fernandes levelled the score again. the draw allowed benfica to remain in second place in group d; koeman was confident he could beat the spaniards at home. on 22 october, benfica hosted estrela da amadora for the primeira liga. two second-half goals by karyaka and then nuno gomes, gave benfica their fifth consecutive win in the competition. four days later, benfica made their portuguese cup debut in the fourth round. playing in estádio do bessa against leixões, simão's decisive performance opened the scoring in the 11th minute and scored benfica's second goal that made the score 2–1. the month ended with an away match against naval. benfica were surprised by the home side and dropped two points in a 1–1 draw, costing them the chance to reach second place. koeman was unhappy with the result, saying benfica played better and deserved to win.