[1][2] Having finished second in the 2018–19 Premier League, Liverpool contested the 2019 FA Community Shield against domestic treble winners Manchester City, losing 5–4 on penalties after a 1–1 draw.

The victory was Liverpool's fourth in the annual contest; only Real Madrid, Barcelona and A.C. Milan have more wins, with five titles apiece.

[4] Liverpool were eliminated in the quarter-finals of the 2019–20 EFL Cup by Aston Villa after fielding a vastly inexperienced side, managed by Liverpool under-23 manager Neil Critchley, while the first-team squad participated in the 2019 FIFA Club World Cup in Qatar under Klopp.

[5] Having finished as runners-up on three previous occasions, Liverpool won their first world title after defeating Brazilian club Flamengo 1–0 in the final after extra time,[6] making them the first English side to win the international treble of the UEFA Champions League, UEFA Super Cup and FIFA Club World Cup.

[7][8] Liverpool were unsuccessful in their defence of the UEFA Champions League, exiting the competition in the round of 16 following a 4–2 aggregate defeat across two legs after extra time to Atlético Madrid.

[16][17] Liverpool also recorded the best ever start to a season in the history of the top 5 leagues in Europe (as they stood in 2020), picking up 20 wins and 1 draw for a total of 61 points out of a possible of 63;[18][19] they eventually extended that record to 26 wins and 1 draw for a total of 79 points out of a possible 81 before suffering their first league defeat on 29 February 2020 to Watford.