This unquestionably happened after Voldemort's downfall - and we also know it probably happened within a year of when the Lestranges and Barty Crouch Jr. were caught for torturing the Longbottoms. This comes from Sirius's statement in GF27 that Crouch Jr. died a year later, and Barty Crouch Sr. lost his popularity and changed jobs. Since he was still running the Wizengamot during this incident, it couldn't have been long after Voldemort's downfall. No doubt Karkaroff was eager to get away from the Dementors.
Karkaroff released from Azkaban
Type of Event Wizarding world
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