Saints have been drawn away to holders Manchester City in the fourth round of the Carabao Cup - in the same week they play there in the Premier League.
Ralph Hasenhuttl's side will make the trip to the Etihad Stadium in the week beginning October 28.
It means they are set to play Pep Guardiola's side away from home twice in the space of four or five days as they are also due to play at the Etihad in the Premier League on November 2.
Manchester City win last year's final against Chelsea on penalties and reached this year's fourth round by winning 3-0 at Preston last night.
It will be the first meeting between the sides in the League Cup since September 1999, when Saints a won a replay 4-3 at The Dell following a goalless draw at Maine Road.
Carabao Cup fourth round draw: Everton v Watford, Aston Villa v Wolves, Manchester City v Southampton, Burton Albion v Leicester, Crawley Town v Colchester United, Chelsea v Man Utd, Oxford v Sunderland, Liverpool v Arsenal.
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