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In the anime Devil May Cry, in one episode, Trish and Lady encounter one another and both already know Dante (who has to stop them from killing one another).

Trish first met Dante in Devil May Cry and Lady in Devil May Cry 3. In Devil May Cry 4, both seem to be in it from what I have read, but neither appear in Devil May Cry 2 before Dante is trapped in the Demon World.

So I am wondering, when does the Devil May Cry anime occur with respect to the timeline of the series?

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The basic answer is "it doesn't" - the anime was not canon to the games. The games' timeline is:

3: Dante is young, hasn't started his agency yet, we meet Virgil as a human (well, half human), he meets Lady.

1: Dante meets Trish and we learn Virgil became Nelo Angelo.

4: Both Lady and Trish are in this.

2: Dante becomes trapped in the underworld and we never learn what happened after because they did a stupid reboot instead of a sequel for DMC 5. These events are not mentioned in other games so it is the final game in the timeline. There are no official canon works that make reference to what happened after.

In the anime he knows both Lady and Trish so it is set after 3 and 1 and before 2. It could be before or after 4 but I would guess before since the anime was made before the game however there's no real answer because, as I said, the anime is not canon to the games.

I don't have links or anything because this is just from my memory - I owned all games (sold my copy of DMC 5) including the DMC 3 Special Edition (where you get to play through Virgil's story), two novels, and have the whole anime on my hard drive and have watched all episodes at least twice.

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In Devil May Cry 5 there is a summary of event which encompasses the anime into the timeline called "History of DMC". according to it the anime happen right after 1 before 2.

Morrison is still the DMC agent as in the anime and Patty is 18 as of DMC 5.

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