For most DLCs you will have to add the winner on Steam, go to that DLC's store page and check if your new "friend" already owns the DLC.
Edit: There are very few DLCs that show up in an user's library.
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Take "Pillars of Eternity - The White March Part I" as an example. It does not show up in your library but you show up as owning the game in store.
"Planetary Annihilation - Digital Deluxe Add-on" is an example (afaik) of a DLC that shows up in libraries.
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Same thing happened to me once. I was looking for winner's unactivated win, SGTools said the winner might not have activated certain game. I checked the winner's library to find none. But when I checked the game's Steam page and under "XX friends already own this game:", he had his name in it.
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DLC's can be a bit irritating to deal with. Even SG Tools has issues checking these.
It's even worse for GoTY, Special Editions and Franchise packs of games or even season passes since the system can't read them for some reason.
Personally, if I see a DLC that I think I have, I check myself. Otherwise, I might remember if I have it or have a season pass.
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Like you do with a winner with a private Steam profile ask for a re-roll so that SG support can check your winner and either advise you to send the DLC or you get the re-roll.
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How can i check a dlc's winner whether s/he has already had this dlc.
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