DaMarcus Beasley had a mediocre performance in a Rangers victory, but the story of the night was American phenom Freddy Adu getting his feet wet in Lisbon as Benfica overcame FC Copenhagen.
Benfica 2 - 1 FC Copenhagen
Freddy Adu made his long awaited European debut as Benfica defeated their Danish opponents at the Estadio de Luz.
The ex-Salt Lake player made his debut in the 38th minute, coming in for an injured Luisao, but would be overshadowed by Portuguese legend Manuel Rui Costa's last-minutes heroics.
Early on, it was Benfica newbie Oscar Cardozo causing problems for the Danes as his header in the 15th minute from a Nuno Assis cross was the first chance of the match. Ten minutes later, his pressure off the ball led to Benfica's first goal.
After intercepting a Copenhagen back pass, the Paraguayan striker fed Manuel Rui Costa, and the ex-Fiorentina man struck a stunning 30-yard missile past Jesper Christiansen to give his club the lead.
The visitors, who would find themselves defending the whole match, equalized just 10 minutes later when a serve from ex-Chelsea man Jesper Gronkjær was cleared poorly by Brazilian Lusiao and straight onto the path of Atiba Hutchinson.
The Canadian hit a first-timer past Benfica keeper Joao Quim, who was unable to stop the close range strike from 10 yards.
Minutes later the young American would make his appearance to a standing ovation, but both teams headed to the locker room with the temporary 1-1 result.
The second half started as the first, with Benfica pushing men up early. Cardozo showcased his shooting ability in the 59th minute by blasting a left-footed shot from 25 yards off a clever near-assist from Rui Costa, but this time Christiansen was up to the task and flew to his right to tip over the ex-Newell Boys long-range effort.
It took some time, but in the 81st minute, Adu finally made his presence felt with a cheer-inducing bicycle kick from outside the box, following a perfect searching ball from the omnipresent Rui Costa. The attempt was more spectacular than the end result, however, as the shot was wayward.
Just when the visitors looked to have sealed the draw, it was Rui Costa who would deliver the winning goal five minutes from time.
The man of the match took a Cardozo pass, and almost standing still, unleashed another impressive right-footed shot past the helpless Christiansen in goal.
The two clubs meet again in two weeks in Denmark, with the series winner advancing to the lucrative Champions League group stage, while the loser receives the consolation prize of dropping into the UEFA Cup.
Rangers 1 - 0 Red Star Belgrade
Rangers managed a 1-0 victory in the opening leg of their Champions League third round qualifying series against Red Star Belgrade, on a night that saw DaMarcus Beasley playing far from his best.
Beasley scored the lone goal in his first European match with Rangers against Zeta, but never looked solid against Red Star, missing a number of passes and coming off midway through the second half. It was his replacement, Nacho Novo, who once again made a case for himself as a Rangers starter with a classy left-footed goal in the 90th minute.
The first half was a cagey one for Rangers as they looked to be concerned, first and foremost, with avoiding giving away the dreaded away goal. They took no serious shots on goal in the half, and their most dangerous chances were all foiled as striker Jean-Claude Darcheville was caught offside time and time again.
Red Star came into this match claiming that they would not settle for a victory on away goals, as they achieved against their last Champions League opponents Levadia Tallin.
The Serbian giants came to attack, and though they may not have produced much in the way of offense, they were certainly aggressive. Filip Dordevic had probably the best chance for the visitors in the 39th minute, surprising the Rangers defense with a beautiful curling effort that ended up just high.
A total of seven Red Star players were booked for yellow cards in this match, while Rangers kept their heads cool and did not see a card.
The Rangers juggernaut continues to roll, with five victories and five shutouts shutouts in their first five competitive matches of the season. Allan McGregor can take little credit for this most recent one, though, as he was never really tested in goal.
The tie continues on August 29 in Belgrade, when we will find out if Novo's last-minute goal could be worth ten million pounds, the estimated value of a Champions League group stage appearance.
[note]Yanks Abroad's Paolo Sarno contributed to this report[/note]