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Europa League finalists Rangers will have to negotiate past Royale Union Saint-Gilloise in the Champions League third qualifying round, where PSV meet Monaco.
Giovanni van Bronckhorst's side entered the qualifying stages through their second-place finish in last season's Scottish Premiership, where winners progress to the play-off stage and losers go automatically into the Europa League group stage.
Rangers also embarked on an impressive run to the Europa League final last season, getting past Borussia Dortmund, Braga and RB Leipzig before being defeated on penalties by Eintracht Frankfurt in Seville.
Union finished second in Belgium's First Division A after a 48-year top-flight absence and will pose a tough task in the two-legged clash, with the first meeting on August 2-3 before the return tie a week later.
Rangers lost at this round to Malmo last year and last made the group stage of UEFA's premier club competition back in 2010-11.
PSV were beaten Europa Conference League quarter-finalists last season, but the team now led by Ruud van Nistelrooy earned a shot at the Champions League after finishing second in the Eredivisie, and will face Monaco.
The Ligue 1 side seemed set to secure group-stage qualification themselves but will have to battle through qualification after they were pipped for second place on the final day of the season by Marseille.
In the other league path fixtures, the winner of Dynamo Kyiv and Fenerbahce will meet Austria's Sturm Graz, while last year's Champions League quarter-finalists Benfica will face either Midtjylland or AEK Larnaca.
The draw for the Champions League play-off round will be on August 1, with those ties taking place over August 16-17 and 23-24.