In a situation when the same team wins both competition, then it is contested between the Singapore Premier League's champions and runners-up.

In the inaugural match, the Singapore Armed Forces defeated Home United 5–4 on penalties following a 1–1 draw.

The Shield first doubled up as the season's opening fixture in 2014 and remained so for all subsequent editions until 2018.

[1]Great Eastern is the co-sponsor for the Community Shield since 2008 and becomes the main sponsor in 2017.

[2] Yeo's is the other co-sponsor for the Community Shield from 2008 until 2016.On 23 February 2019, the Football Association of Singapore (FAS) announced that AIA Singapore as the new title sponsor of the Singapore Premier League and Community Shield as part of a two-year agreement.