Turkey's Galatasaray faces an uphill battle to progress in the UEFA Europa League after a home 2-1 defeat by Portugal's Benfica.
Benfica was awarded a penalty in the 26th minute following a controversial handball by Galatasaray's Marcao. Eduardo Salvio converted the penalty.
In the second half, the Lions' new transfer Christian Luyindama equalized in the 54th minute but Haris Seferovic secured Benfica's win with a goal 10 minutes later.
Galatasaray is the only Turkish club to have won the UEFA Cup in 1999-2000 and the 2000 UEFA Super Cup, while Benfica won two European Cups in 1961 and 1962 and lost two Europa League finals in 2013 and 2014.
Galatasaray and Benfica were among the eight teams dropping from the Champions League group stage to the Europa League.
The second leg will be played Feb. 21 in Lisbon, Portugal.