Liverpool scraped into the group stages of the Champions League courtesy of a 118th-minute goal from Dirk Kuyt against a valiant Standard Liege.
Kuyt sidefooted home at the far post to end a tortuous night for the Reds.
They survived two early scares when keeper Pepe Reina produced superb saves in palming away strikes from Dieudonne Mbokani and Marouane Fellaini.
Liverpool were denied a penalty in extra-time when Oguchi Onyewu brought down Nabil El Zhar before Kuyt's goal.
The result and timing of the goal was harsh on the Belgian champions, who had proved stubborn opponents for Liverpool.
The Reds had been fortunate to leave Liege with a goalless draw in the first leg and were expected to show an improvement on home territory.
But the visitors had other ideas as they were inspired rather than overwhelmed by the occasion and quickly caused the Anfield side problems.
Mbokani left fly from 22 yards and Reina, who saved a penalty in Belgium, had to smartly dive low to his right to turn the ball around his post.
The chance added to Liverpool's nerves and, after Robbie Keane poorly shot over, Liege continued to increase the sense of anxiety around Anfield.
Igor De Camargo missed a cross with an attempted shot but recovered to put the ball back in for Fellaini, whose steered volley was palmed away by Reina.
The Spanish keeper was again proving Liverpool's saviour and, despite Xabi Alonso curling an effort wide for the Reds, the pressure and pace of Liege had the home team looking shaky.
And the surge of confidence sweeping through the visitors was signalled when Marcos Camozzato angled an ambitious 35-yard half-volley wide.
Liverpool's lack of width was being exposed by the Belgian champions, who comfortably closed out the home side's attempted attacks through the middle.
When the Reds did have a sight on goal from a corner, Kuyt headed a far post header disappointingly wide just before the interval.
Liege sat back after the break and held Liverpool at bay as they hoped to catch the Merseysiders out on the counter-attack.
The game became a more cagey affair as the Reds continued to struggle to find a way through their resolute opponents.
Liverpool were then left breathing a sigh of relief when De Camargo sent a diving header just wide before the end of 90 minutes.
In extra-time, Alvaro Arbeloa had an audacious long range half-volley saved by keeper Rorys Aragon before Onyewu survived giving away a spot-kick.
Kuyt then struck, as penalties loomed, for a goal on his 100th appearance for the club to put them into Thursday's lucrative group stage draw.
Liverpool boss Rafael Benitez:"We have to give credit to Kuyt because sometimes when he makes a mistake people highlight it.
"But you could see for the 120 minutes how hard he works and he is an amazing player for every team.
"He never hides and is the kind of player who is very important and he is a fantastic professional."
Standard Liege boss Laszlo Boloni: "We are very sad after that result. Over two matches we have been the best organised team and we deserved better than to lose like that in the final minutes.
"We have produced a high standard in both matches, and now I hope that can be continued in our league matches and the Uefa Cup.
"I sometimes wondered whether the referee was affected by the fact that we were playing a big team. I felt we should have had a couple of penalties.
"But in the end we created a lot of good situations in both matches and did not make use of them."
Liverpool: Reina, Arbeloa, Carragher, Skrtel, Aurelio, Kuyt, Gerrard, Alonso, Benayoun (Babel 61), Keane (El Zhar 83), Torres (Plessis 120).Subs Not Used: Cavalieri, Dossena, Agger, Spearing.
Goals: Kuyt 118.
Standard Liege: Aragon, Camozzato, Onyewu, Sarr, Dante, Dalmat (Jovanovic 86), Fellaini, Defour (Nicaise 118), Witsel, De Camargo (Toama 101), Mbokani.Subs Not Used: Devriendt, Goreux, Mikulic, Ingrao.
Booked: Sarr, De Camargo, Dante.
Ref: Massimo Busacca (Switzerland).