Liverpool conceded three counter-attack goals in a 4-2 pre-season friendly defeat to AC Milan in Hong Kong.
The Premier League champions were constantly hit on the break by the Serie A side, with Rafael Leao, Ruben Loftus-Cheek and Noah Okafor all taking full advantage of Liverpool’s vulnerability.
Reds boss Arne Slot fielded experimental backlines in both halves as Ryan Gravenberch started alongside Virgil van Dijk, who could not stop Leao’s cracking breakaway opener in the 10th minute.
But Liverpool were level 16 minutes later through Dominik Szoboszlai’s piece of magic as he clipped a stunning equaliser into the top corner.
British-record £116m summer signing Florian Wirtz, operating in a false nine role, and 16-year-old Rio Ngumoha, who caused Milan problems on the left, impressed in the first half.
Gravenberch was the only starting player to remain on the pitch for the start of the second half as Slot rang the changes, but his side were caught cold on the break once again as Leao burst free to set up Loftus-Cheek for a low finish.
Just seven minutes later, Milan’s Alexis Saelemaekers exposed Liverpool again to tee up Okafor for a clinical first-time sweeping finish.
Cody Gakpo gave Liverpool slim hope of a dramatic comeback with a fine 93rd-minute stoppage-time header from Ibrahima Konate’s cross.
But just a minute later, a calamitous mix-up between new goalkeeper Giorgi Mamardashvili and defender Kostas Tsimikas allowed Okafor to easily roll home into an empty net and inflict Liverpool’s first loss this summer.
Liverpool’s pre-season continues with a trip to Yokohama F. Marinos in Japan on Wednesday (11.30am UK time).
What’s next for Liverpool?
Wednesday: Yokohama F. Marinos – Nissan Stadium, Yokohama, 11.30am
August 4: Athletic Club (double header) – Anfield, kick off 5pm and 8pm
August 10: Crystal Palace (Community Shield) – Wembley, kick-off 3pm
August 15: Bournemouth (Premier League) – Anfield, kick-off 8pm, live on Sky Sports