Rangers will face German side Borussia Dortmund in the Europa League knockout round play-off.
The Scottish champions were seeded in Monday’s draw having finished runners-up in their group behind Lyon.
Dortmund, who sit second to Bayern Munich in the Bundesliga, dropped into the Europa League after finishing third in their Champions League section.
The first legs will be played on 17 February, with the second legs held a week later.
This season’s new format means that the eight group winners, including West Ham United, directly advance to the round of 16.
Rangers last met Dortmund in the third round of the 1999-2000 Uefa Cup, when the Germans went through on penalties after both sides won their home legs 2-0.
Since then, the Glasgow side have won two, drawn one and lost five games against German opposition.
They shared 2-2 draws in both games with Dortmund in their Champions League group in 1995-96, while Rangers prevailed on aggregate in the 1966-67 European Cup-winners’ Cup and 1982-83 Uefa Cup.
The current Dortmund side, managed by Marco Rose after he switched from Borussia Moenchengladbach this summer, only missed out on progressing to the Champions League knock-out stage via head-to-head goal difference with Sporting Lisbon as both finished well adrift of Ajax.
Celtic, Leicester City and Tottenham Hotspur are involved in the Europa Conference League knockout round play-off draw starting at 13:00 GMT.
Europa League knockout round play-off draw
Sevilla v Dinamo Zagreb
Atalanta v Olympiakos
RB Leipzig v Real Sociedad
Barcelona v Napoli
Zenit St Petersburg v Real Betis
Borussia Dortmund v Rangers
Sheriff Tiraspol v Braga
Porto v Lazio