Liverpool's record signing, Florian Wirtz, made his first start for the club as Arne Slot's team suffered a 4-2 defeat against AC Milan at the packed Kai Tak Stadium in Hong Kong.
Darwin Nunez and Luiz Diaz were notably absent from the Reds' squad amid rumors of their potential departure following the arrival of Hugo Ekitike and the club's pursuit of Newcastle United's Alexander Isak.
Before the match, Liverpool legend Sir Kenny Dalglish laid a wreath of flowers, and the players wore a 'Diogo J 20' emblem on their shirts to honor their former teammate Diogo Jota, who tragically passed away in a car accident earlier this month.
Despite dominating the opening 10 minutes, it was AC Milan who took the lead when Rafael Leao scored past Alisson Becker following a swift counter-attack.
Dominik Szoboszlai equalized with a superb curling shot into the top corner of Mike Maignan's goal from the edge of the box.
England midfielder Ruben Loftus-Cheek restored Milan's lead early in the second half as Liverpool's defense was caught off guard, and Noah Okafor extended the lead to 3-1 with a brilliant finish past Liverpool's new goalkeeper, Giorgi Mamardashvili.
Cody Gakpo managed to pull one back in added time with a header from Ibrahima Konate's precise cross, but a mix-up between Mamardashvili and Kostas Tsimikas allowed Okafor to score his second goal.
Liverpool will now travel to Japan to face Yokohama F. Marinos on Wednesday.
Wirtz Comfortable in Unusual Role
Florian Wirtz, a £116 million acquisition from Bundesliga's Bayer Leverkusen, played an unfamiliar false nine role against Milan, with Nunez and Diaz absent and newcomer Ekitike not yet ready to play.
The German playmaker was flanked by the promising 16-year-old Rio Ngumoha on the left and Mohamed Salah in his customary right-wing position.
Slot is expected to deploy Wirtz as either an attacking midfielder behind the striker or a narrow left-sided forward, but in Hong Kong, he demonstrated his ability to link the forward line from an advanced central position.
His quick thinking and deft first touch consistently kept him ahead of his opponents, allowing him to drive forward with the ball.
Fans were disappointed when he did not return for the second half, but they got a glimpse of Liverpool's other new signings, right-back Jeremie Frimpong and left-back Milos Kerkez, who were introduced at halftime.
Liverpool Look Short at the Back
News emerged before the match that versatile defender Joe Gomez had returned to England for treatment on an Achilles injury, leaving Liverpool with only two fit senior center-backs.
Liverpool's defense appeared vulnerable in both halves, with Virgil van Dijk starting the first period and Ibrahima Konate replacing him in the second.
In Gomez's absence, Ryan Gravenberch partnered with Van Dijk in central defense, leaving the usual midfield shield missing.
With Jarell Quansah's transfer to Bayer Leverkusen, Liverpool is already short on central defenders. Andrew Robertson was used as a center-back in a pre-season win at Preston North End, and now another left-back, Tsimikas, had to fill in.
With only 12 months remaining on his contract, Liverpool has been linked with a move for Crystal Palace and England defender Marc Guehi this summer, and Gomez's injury could heighten that interest.