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.
Man United could be without Toone until new year, says Skinner
Marc Skinner revealed that Manchester United could be without midfielder Ella Toone until the new year after she picked up a calf injury in training.
Toone has featured in five games in the Women's Super League this season, but is yet to register a goal or an assist so far this term.
The 25-year-old has missed United's last two games and was not selected in Sarina Wiegman's England squad for their upcoming friendlies against the United States and Switzerland.
She had previously appeared in a staggering 96 straight matches before missing United's WSL showdown with Leicester City last weekend.
But ahead of the Red Devils' meeting with league leaders Chelsea on Sunday, Skinner confirmed they would be without Toone for not only that game, but for the foreseeable future.
"We have three games [after the international break and before Christmas]. There's always the hope, but I think you balance and you go, 'right, if we can get her back, we get her back'," Skinner said.
"But we're just not going to rush her in this moment because it's a calf injury, it's your running mechanism. If we injure the running mechanism, it takes longer.
"So ideally we'd like her back for those games afterwards.
"The projection is she misses this game [Chelsea], she misses the international window, probably misses the first game after that, and then we'll see from there.
"But because it is such a short block of only three games, we'll assess whether it's worth that or actually resetting to come back after Christmas."
Al-Nassr 1-2 Al-Qadsiah: Aubameyang winner ends hosts' unbeaten run
Pierre-Emerick Aubameyang hit the winner as Al-Qadsiah inflicted a 2-1 defeat on Al-Nassr in the Saudi Pro League on Friday to end their 21-match unbeaten run.
Cristiano Ronaldo's seventh league goal of the season put Al-Nassr ahead, but Al-Qadsiah replied swiftly through Julian Quinones before Aubameyang struck the decisive blow.
The hosts drew first blood in the 32nd minute when Ronaldo slotted home after Al-Qadsiah goalkeeper Koen Casteels had spilled a routine catch from Talisca's cross.
However, Al-Nassr's joy was short-lived when Quinones brought down Turki Al Ammar's delivery five minutes later, with the Mexcio winger firing past Bento to level the scores.
Quinones also played a part in the winning goal after brilliantly turning the ball back across goal from Nahitan Nandez's search pass to tee up a simple finish for Aubameyang.
The result sees Al-Qadsiah move level on 22 points with third-placed Al-Nassr, with Al-Shabab also level with them.
Stefano Pioli's Al-Nassr are six points adrift of defending champions and leaders Al-Hilal, who also have a game in hand.
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