In 2019–20, Cuadrat took the team back to the playoffs in the Indian Super League for a third consecutive season, being the only club in the Indian Super League to reach the playoff in every appearance. The feat also made Bengaluru FC the first team to reach the playoff as defending champions, since ATK in the 2015–16 edition of the tournament. Defending champions had failed to make it to the top four the following season, with ATK (in 2015) and Bengaluru FC (in 2020) the only teams to do so. However, it was ATK that stopped Bengaluru's charge to the final with an aggregate win of 3–2 in the playoffs. The Kolkata side would go on to claim the title, winning 3–1 against Chennaiyin FC in the final.
