In the summer of 2019, Ricketts made more notable signings to strengthen the squad for the upcoming 2019–20 season, bringing in players such as Jason Cummings from Nottingham Forest, Sean Goss from Queens Park Rangers, Donald Love from Sunderland, Ethan Ebanks-Landell from Wolves and Aaron Pierre from Northampton Town. Ricketts started the season with a 1–0 win at home to Portsmouth on 4 August, with loanee Ryan Giles scoring the goal. During the 2019–20 season, Ricketts lead the club to the fourth round of the FA Cup for the second time during his management spell, defeating Bradford City, Mansfield Town and Bristol City along the way. The fourth round would see Ricketts and his Shrewsbury side host Premier League leaders and European and World champions Liverpool, where Shrewsbury came from 0–2 down to draw 2–2 with 2 goals from substitute Jason Cummings, forcing a replay at Anfield. In the replay, Shrewsbury fell short after a Shaun Whalley goal was disallowed by VAR for offside and an own goal from Ro-Shaun Williams saw the hosts win 1–0. This cup run brought repercussions, however, as Ricketts and the club went 10 league games without a win between December 2019 and February 2020. A 0–2 home defeat to Accrington Stanley on 11 February 2020 followed by another 2–0 defeat away at Portsmouth on 15 February put Ricketts' job under severe pressure. The winless run ended a week later on 22 February after a 1–0 win at home to Doncaster Rovers. On 14 March 2020, Ricketts and his Shrewsbury side were scheduled to take on top-of-the-table Coventry City at St Andrew's, however the match was postponed due to the outbreak of COVID-19. Due to the pandemic, the 2019–20 League One season was cut short and it was decided that final league positions would be based on a points-per-game basis. This saw the club finish 15th in the final table.