In 1995 Paul Gascoigne was in the Rangers side that drew 2-2 with the Germans.
Rangers will face a German team in the knockout round.
The Scottish champion were placed in the top spot in Monday's draw, having finished runners-up in their group.
After finishing third in the section of the competition, they dropped into the Europa League.
The first legs will be played on 17 February, with the second legs held a week later.
Man Utd will face Paris Saint-Germain.
The new format means that the eight group winners, including West Ham United, will advance to the round of 16.
In the third round of the 1999-2000 Uefa Cup, Rangers and the Germans went to penalties after both teams won their home legs.
The Glasgow side has lost five games against German opponents.
In the 1995-96 season, they shared 2-2 draws with the German team in the group stage of the European Cup, while Rangers won the 1966-67 European Cup and 1982-83 Uefa Cup.
Marco Rose's current side missed out on progressing to the knockout stages of the European competition, despite finishing well ahead of their rivals.
The draw for the play-off round of the Europa Conference League will take place at 13:51.
The play-off draw for the knockout round.
Sevilla vs Dinamo Zagreb.
Atalanta is playing Olympiakos.
Real Sociedad vs RB Leipzig.
Barcelona is playing Napoli.
Zenit St Petersburg is playing Real Betis.
The game is between the Rangers and Borussia Dortmund.
Sheriff Tiraspol vs.
Lazio vs Porto.
