Liverpool's first taste of the real thing in Europe failed to produce the confidence-boosting start they wanted and had it not been for another Michael Owen goal it could have been an embarrassing night.
In the end it was just pure frustration. They ran into a committed and well-organised side in Portuguese champions Boavista and will have hopefully learned a profound lesson from the experience.
Boavista had stolen their domestic crown from big time neighbours Porto last season, and almost stole away with the spoils at Anfield. They were ahead on three minutes through Elpideo Silva, and only allowed Owen one glimpse of goal all night.
And he took it superbly. It was his 12th for club and country this term as he coolly clipped home after Emile Heskey's pass.
From then on Liverpool wanted desperately to throw it all forward, but knew they dare not against such pace and guile. Their first exposure to the elite they have craved exposed some of their problems.
The pace is not what it was at the back, Heskey struggled with the ball continually pumped at him, and the night drifted away from Liverpool, who now need to get something next week from a tougher assignment in Dortmund.
Liverpool came into the game on the back of a wretched display in losing to Aston Villa on Saturday and boss Gerard Houllier's response was to recall Michael Owen and Danny Murphy along with French teenager Gregory Vignal. Out went Robbie Fowler, Nick Barmby and John Arne Riise. Liverpool started with Steven Gerrard restored to his England central midfield position and they were wearing a special new Champions League shirt based on the one they wore back in the glory days of the 1970s and 1980s - but it did not stop them going behind after three minutes.
Vignal was penalised deep in the Portuguese half for a mild pull. The punishment was severe. Goalkeeper Pereira took the free-kick and pumped it into Liverpool's area. Their inability to clear this sort of ball, already evident this season, manifested itself again as Alexandre Goulart headed down and Elpideo Silva drove the ball into the roof of the net from eight yards.
Boavista played a very fluid 4-3-3 with Silva's pace a constant threat up front with Carlos Duda equally dangerous.
Owen was tightly marked by Paulo Turra, one of six Brazilians in the Boavista side, with the treatment of Heskey, uncompromising to say the least.
Jerzy Dudek got the chance to show why Houllier has bought him with a brilliant one-handed save to his right from a Goulart header on the run.
Owen and Heskey were tracked everywhere, but the one moment they were given a yard, Liverpool equalised on 28 minutes.
Heskey took possession and spun to send Owen clear, his pace taking him away from the defence and he made no mistake with a careful right-footed curler from the edge of the box over Ricardo.
Boavista punished mistakes instantly and they came frequently when Liverpool kept giving the ball away. First Hamann and then Vignal in quick succession were exposed and the end of the move was a drilled crosshot from Duda that flashed past Dudek's right-hand post.
Boavista found themselves being forced back after the break, but were still dangerous on the break. But Liverpool's chances were rare. A Gerrard 25-yard right-footed free-kick flew past the far post on 60 minutes and then Heskey saw a close-range header drift wide.
Silva again hooked over from Goulart's touch down with Liverpool's defence watching. The danger was still very real.
Duda fired wide and Dudek had to save bravely at Pedro Santos' feet, Liverpool living on a knife edge as they sought the one vital breakthrough.
On 70 minutes Riise came on for Murphy, resulting in McAllister switching to the right flank while the young Norwegian moved to the left.
Boavista clocked up the bookings, five in the final minutes, as they defended magnificently, skipper Emanuel and Brazilian Turra outstanding.
Liverpool fought and strained for the breakthrough, but their game lacked variety and that elusive spark.
LIVERPOOL: Dudek, Carragher, Henchoz, Hyypia, Vignal, Gerrard, McAllister, Hamann, Murphy (Riise 71), Heskey, Owen. Subs Not Used: Arphexad, Fowler, Redknapp, Barmby, Biscan, Litmanen. Booked: Vignal. Goals: Owen 29.
BOAVISTA: Ricardo, Frechaut, Turra, Emanuel, Erivan, Petit, Alexandre, Glauber, Sanchez (Pedro Emanuel 59), Duda (Bosingwa 84), Silva (Serginho 79). Subs Not Used: William, Loja, Gouveia, Marcio. Booked: Turra, Silva, Emanuel, Glauber, Ricardo, Petit, Pedro Emanuel. Goals: Silva 3.
Referee: Kyros Vassaras (Greece).
