Jurgen Klopp's side come from behind twice against Arsenal but still lost the game as Bukayo Saka scored a late penalty to grab a 3-2 win.
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It continued their poor start to the season with the Reds winning just two of their opening eight games.
To make matters worse, both Luis Diaz and Trent Alexander-Arnold are seemingly set for spells on the sidelines.
Diaz had to be substituted before the break with an apparent knee injury, while Alexander-Arnold did not return for the second half due to an ankle problem.
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Diaz was then seen leaving the Emirates on crutches with his knee in a brace.
Liverpool boss Klopp then gave a downbeat assessment of the injuries to the pair.
He told his post-match press conference: "Lucho [Diaz] we had to change before [half-time]. [It's] something with the knee, not good.
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"He will have a scan and then we will know more. I have no idea about the extent and then on top of that Trent is bad as well with the ankle.
"[He] twisted the ankle, not good. Trent never, in seven years, went off if he could have played on. He was in too much pain, it started swelling immediately, so we will have to see."
Liverpool are already 14 points off league leaders Arsenal, while they face reigning champions Man City at Anfield on Sunday.