Liverpool's record signing Fernando Torres and another new addition Yossi Benayoun both missed spot kicks to hand Portsmouth the Asia Trophy after a 4-2 penalty shoot-out victory at Hong Kong Stadium.
A goalless yet entertaining game could not be settled in 90 minutes and Niko Kranjcar scored the decisive spot-kick to ensure Pompey's triumph.
Liverpool were the first to gain a measure of control after a full-blooded opening and Dirk Kuyt flicked a Harry Kewell cross narrowly over the crossbar after nine minutes.
Kuyt then brought a smart save out of David James down to his left on 20 minutes after the Dutchman had run across the line to latch on to Jermaine Pennant's reverse pass.
New signing Ryan Babel then almost embarrassed James when he robbed the goalkeeper of possession but the Portsmouth defence eventually scrambled the ball to safety.
Liverpool came closest to taking the lead five minutes later, however, as Babel probed on the edge of the area before laying the ball off to Xabi Alonso.
The Spain midfielder moved the ball out to Pennant on the right and the winger easily beat Matt Taylor before crossing to the near post for Kuyt to power a header goalwards.
However, James reacted smartly to somehow keep the ball out on the line with his legs.
Gary O'Neil could then have put Pompey in front seven minutes before the break as Sulley Muntari's through-ball set the midfielder free but Jose Reina narrowed the angle well and deflected his effort wide for a corner.
Torres made his long-awaited bow in the tournament after 51 mins to rapturous applause when he replaced Kewell.
Six minutes later, Mohamed Sissoko's raking ball found Pennant on the left and the winger bundled his way past the onrushing James but sliced horribly wide.
Kuyt then spurned yet another opportunity when he decided to cut back onto his right foot instead of taking Sylvain Distin on and his shot was off-target before Torres blazed a good opportunity over the bar on 65 minutes when Kuyt's pass, intended for John Arne Riise, ricocheted off Sol Campbell and fell to the Spaniard inside the box.
A good interchange between Pennant and Sissoko saw Torres fire wide before Reina's piercing kick sent the striker clear and although the chance looked lost after Campbell had held him up, he still managed to stab a loose ball goalward that James did well to parry.
Muntari was then booked for clattering Steve Finnan before Steven Gerrard was introduced five minutes from time for Pennant.
Reina had to be quick off the mark to close down John Utaka after the goalkeeper's poor clearance had landed his side in trouble and James smothered well at Kuyt's feet after the Dutchman had linked well with Torres.
The Spaniard saw his penalty saved by James in the shoot-out as he gave away the advantage gained by Utaka dragging Portsmouth's first penalty well wide of Reina's right-hand post.
Benayoun was also denied by James before Kranjcar dispatched his spot-kick to seal the win.