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Midnight Pathlighter says:

"Whenever one or more creatures you control deal combat damage to a player, venture into the dungeon"

If I attack with two creatures at two different players and they both deal combat damage to those players, do I get two venture triggers?

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Yes, you get one trigger per player hit.

As Midnight Pathlighter itself demonstrates, there is a distinction in wording between "a (something)" and "one or more (something)". If the wording is just "a (something)", it counts every single instance of the thing, rather than grouping them together. So you will indeed get multiple triggers of Midnight Pathlighter if you hit multiple opponents.

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    To demonstrate the "a" vs "one or more" distinction with this card, if you attack 2 players with a total of 4 creatures, you still only get 2 triggers.
    – murgatroid99
    Jul 30, 2021 at 16:41

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