This was billed jokingly as the Philippe Clement Derby, with the former Rangers and Brugge boss reportedly watching on from the stands.
By full-time, however, there was little humour left in Ibrox as Rangers all but handed their Belgian visitors a commanding advantage.
Russell Martin handed a debut to 19-year-old Jayden Meghoma, with Hamza Igamane and Thelo Aasgaard among the substitutes.
The hope before kick-off was simple: keep the tie alive for next week. Within 20 minutes, that already looked fanciful.
A horror-show opening saw Brugge gifted three goals. First, a calamitous mix-up between Nasser Djiga and goalkeeper Jack Butland left Romeo Vermant lobbing into an empty net.
Then, woeful zonal marking allowed Jorne Spileers to tap home from a corner. Moments later, Rangers failed to clear their lines and Brandon Mechele lashed in a third from the edge of the box.
3-0 down before the half-hour mark, the boos rang loud and Ibrox emptied before half-time.
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Rangers improved after the break, largely through the energy of Djeidi Gassama down the left. It was his link-up with Meghoma that created the lifeline, Danilo turning in from close range on 50 minutes.
Suddenly there was some fight. Mohammed Diomande should have added another, Gassama went close, and Rangers even thought they had a second when the former Sheffield Wednesday winger bundled past Simon Mignolet, only for VAR to harshly rule it out for a foul.
Despite flashes of life, Brugge always carried threat, and Butland was called on repeatedly to prevent the scoreline worsening.
By the final whistle, the damage was already done: a 3-1 defeat that leaves Rangers with a mountain to climb in Belgium.
The positives? Gassama looked electric, Meghoma showed glimpses on debut, and there was at least some spirit after the break.
But make no mistake – this result has been coming. The defending was shambolic, the midfield passive, and Martin now knows that Ibrox is a very different beast to MK Dons, Swansea or Southampton.
Unless Rangers summon one of those fabled European miracles, the Champions League dream is slipping away once again.