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It is never clearly stated when the Federation made first contact with the Cardassians. The first episode with the Cardassians takes place in 2367. In this episode it is stated that a long war between the Federation and Cardassia had ended about a year ago.

In the alternate timeline, in the new movie, first contact seems to have taken place by the 2250s, because Uhura orders a Cardassian drink.

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