| Hong Kong Senior Challenge Shield | |
| Year: | 2005–06 |
| Country: | Hong Kong |
| Num Teams: | 8 |
| Champions: | Kitchee |
| Count: | 5 |
| Runner-Up: | Happy Valley |
| Matches: | 7 |
| Goals: | 15 |
| Prevseason: | 2004–05 |
| Nextseason: | 2006–07 |
The Hong Kong Senior Shield 2005–06, also known as the 2005/2006 HKFA Senior Shield, is the 105th staging of the Hong Kong's oldest football knockout competition.
The competition started on 4 March 2006 with 8 Hong Kong First Division League clubs and concluded on 18 March 2006 with the final.
Kitchee captured their 5th title of the competition after beating Happy Valley by 3-0 in the final.
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Keith Gumbs of Kitchee
Lico of Xiangxue Sun Hei
Kwok Yue Hung of Kitchee Clodoaldo de Oliveira of Happy Valley
Stephen Joseph Musah of Dongguan Lanwa André of Xiangxue Sun Hei Fábio Lopes Alcântara of Happy Valley Evanor of Happy Valley Keith Gumbs of KitcheeEach player received a prize of HK$5,000.[1]