On October 29 Beijing time, Chelsea drew 1-1 with Liverpool away from home in the fourth round of the English League Cup. They then lost 5-6 in the penalty shootout and were eliminated.
This was the fifth time the two sides had settled a competitive match in a penalty shootout, with Chelsea losing on all five occasions. Before this match, Chelsea had already lost four penalty shootouts to Liverpool.
The two sides first met in a penalty shootout in the 2007 Champions League semi-final, with Chelsea losing 4-1. Chelsea suffered another shootout defeat in the 2019 UEFA Super Cup, losing 5-4.
In 2022, the two sides met in the League Cup and FA Cup finals, with Chelsea losing on penalties 11-10 and 6-5, respectively. Facing Liverpool again, Chelsea once more lost the shootout, missing out on a place in the League Cup quarter-finals.