Last season, it was Paul Tisdale's turn to face Jurgen Klopp's Liverpool with Exeter City, this campaign will give Derek Adams to do so as Plymouth Argyle manager after the Pilgrims defeated Newport County.
A Graham Carey penalty deep into extra time - after David Goodwillie had been fouled - proved to be enough for Argyle, as they came out on top in the tie which saw the League Two leaders defeat the division's bottom-placed club.
It was Carey's tenth goal of the campaign and it ensure that the Pilgrims will feature in the FA Cup third round for only the second time since 2010. His effort sets up what will be the 11th meeting between Argyle and the Reds, the last of which occurred in the 1961-62 season.