The 2025 MLS Cup Playoffs are coming down to the wire, with big names a-plenty including Lionel Messi and Heung-min Son chasing postseason glory.

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Messi’s Inter Miami won a Supporters’ Shield last season but came up just short in 2025. They can make amends with their first MLS Cup in just a few weeks time.

Son’s LAFC are bidding to return to the MLS Cup Final for the third time in four seasons, three years removed from beating this season’s Supporters’ Shield winner, the Philadelphia Union, in the 2022 final.

Both trophies have terrific histories, and this post deals with both of them.

All-time MLS Cup Finals, winners

1996: DC United defeat LA Galaxy 3-2 aet

1997: DC United defeat Colorado Rapids 2-1

1998: Chicago

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