Panathinaikos’ visit will mark Russell Martin’s first competitive game as Rangers head coach and the former Southampton boss has been handed the toughest of their possible draws despite the Ibrox side having been seeded.
All three potential opponents were, like Rangers, runners-up in their domestic leagues, but while the Greek side are 111th in the European club rankings, 86 places behind Rangers, Swiss side Servette are 139th (one behind Heart of Midlothian) and Norwegians Brann 189th.
Panathinaikos have never lost to Scottish opponents over 90 minutes in four meetings with Rangers, two with Motherwell and one with Aberdeen, winning four of their seven games.
However, it was Rangers who progressed when they last met the Ibrox side.
Having beaten Aberdeen 3-0 at home in the 2007-08 Uefa Cup group stage, the Greeks exiting on away goals after a 0-0 stalemate in Glasgow was followed by a 1-1 draw in Athens in the round of 32.
They had beaten Rangers 3-1 at Ibrox, and drew 1-1 at home, in the Champions League group stage in 2003, while they eased aside Motherwell 5-0 on aggregate in their latest meeting with a Scottish side in 2012 – in the Champions League third qualifying round.
Panathinaikos have not reached the Champions League proper since 2010-11 and last season started in Europa League qualifying, beating Botev Plovdiv but losing to Ajax before qualifying for the Conference League by defeating Lens.
They lost 4-1 at home to eventual winners Chelsea and beat The New Saints 2-0 in Wales in the new league stage, finishing 13th, before beating Vikingur Reykjavik in the knockout phase then losing to Fiorentina in the last 16.
Rangers lost their opening Champions League qualifier to Dynamo Kyiv last season under Philippe Clement, but reached the Europa League quarter-finals, by which time interim head coach Barry Ferguson was in charge.
Teams winning their second qualifying round ties face two more rounds to make the league stage.