2008–09 Hong Kong Senior Challenge Shield
| Country |
 Hong Kong
|
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|---|---|---|---|
| Teams | 13 | ||
| Defending champions | Eastern | ||
| Champions | TSW Pegasus | ||
| Runners-up | Convoy Sun Hei | ||
| Matches played | 12 | ||
| Goals scored | 35 (2.92 per match) | ||
| Attendance | 20,625 (1,719 per match) | ||
| Top goal scorer(s) |
 Guy Junior Ondoua (TSW Pegasus) (6 goals) |
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| Best player |
 Itaparica(TSW Pegasus) |
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Hong Kong Senior Challenge Shield 2008–09, officially named as Eisiti Senior Shield (Chinese: 上清飲高級組銀牌) due to the competition's sponsorship by Shenzhen Xiangxue Eisiti FC, was the 107th season of one of the Asian oldest football knockout competition, Hong Kong Senior Challenge Shield. It was a knockout competition for all the teams of Hong Kong First Division League. The winner would qualify for AFC Cup 2010, if it was a full member of The Hong Kong Football Association.
The final match was held in Hong Kong Stadium on 21 December 2008. The tournament was won by TSW Pegasus, who beat Convoy Sun Hei 3–0 in the final, thanks to two goals from Guy Junior Ondoua and one from Beto. Since TSW Pegasus was not a full member of the Hong Kong Football Association, the AFC Cup 2010 qualification of it was not confirmed before the final of 2008–09 Hong Kong FA Cup.
All times are local (UTC+8).
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