2019–20 Hong Kong Senior Challenge Shield is the 119th season of the Hong Kong Senior Shield. 10 teams entered this edition, with 2 games being played in the first round before the quarter-finals stage. The competition was only open to teams that played in the 2019–20 Hong Kong Premier League.
The champions received HK$150,000 in prize money while the runners up received HK$50,000. The MVP of the final received a HK$10,000 bonus.
The final of the Senior Shield was originally held on 9 February 2020, but was postponed to 2 October 2020 and was played behind closed doors due to the 2020 coronavirus pandemic in Hong Kong.
Kitchee were the defending champions, but were eliminated in the quarter-finals. Eastern became the champions for the 11th time after beating Lee Man in the final.