| Hong Kong Senior Shield | |
| Year: | 2019–20 |
| Country: | Hong Kong China |
| Num Teams: | 10 |
| Dates: | 21 September 2019 – 2 October 2020 |
| Champions: | Eastern |
| Count: | 11 |
| Runner-Up: | Lee Man |
| Matches: | 9 |
| Goals: | 33 |
| Top Goal Scorer: | Everton Camargo (4 goals) |
| Player: | Everton Camargo |
| Prevseason: | 2018–19 |
| Nextseason: | 2022–23 |
2019–20 Hong Kong Senior Challenge Shield is the 118th 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.
| Stage | Round | Draw Date | Date | Matches | Clubs |
|---|---|---|---|---|---|
| Knockout | First Round | 12 September 2019 [1] | 21 September 2019 | 2 | 10 → 8 |
| Quarter-finals | 9–10 November 2019 | 4 | 8 → 4 | ||
| Semi-finals | 25–26 December 2019 | 2 | 4 → 2 | ||
| Final | 2 October 2020 at Mong Kok Stadium | 1 | 2 → 1 |
Bold = winner
* = after extra time, = penalty shootout score
| Rank | Player | Club | Goals[2] |
|---|---|---|---|
| 1 |  Everton Camargo | Eastern | 4 |
| 2 | Gil | Lee Man | 3 |
 Michael N'dri | Lee Man | ||
| 4 |  Jonathan Acosta | Lee Man | 2 |
 Giovane | R&F |