The ill-fated Rangers reign of Portuguese manager Pedro Caixinha is a period in Ibrox history most fans want to forget but one of his most prominent failed signings is earning Champions League retribution.
Fabio Cardoso has gone from being released by Rangers to playing against Liverpool in the most prestigious club football competition on planet Earth.
The ex-Rangers defender was pitched in against the Reds for new club FC Porto in a Champions League debut he might want to forget.
Not only was this Cardoso’s first game in European football’s elite competition, but it’s his first game for FC Porto since joining the club in the summer.
Despite the match being played at the Estadio do Dragoes, Porto were resoundingly beaten 5-1 by a rampant Jurgen Klopp side.
Now 27, Cardoso was thrust into the starting line-up following an injury to Portuguese war-horse Pepe in the warm-up to the match.
A Sadio Mane strike sandwiched between a Mo Salah double had Liverpool 3-0 up before Mehdi Taremi pulled one back with 15 minutes to go.
However, enter Bobby Firmino who scored two goals in four minutes to put some gloss on the result as Liverpool blew the Portuguese club away in Porto.
Fabio Cardoso will certainly have better games but for Rangers fans the defender will always be remembered for what might’ve been at Ibrox.
A £1.5m signing for Vitoria Setubal, the defender toiled with the physicality of life in Scotland as Pedro Caixinha’s ill-fated reign came crumbling down.
Eventually released in July 2018, the player would go on to have three successful seasons with Santa Clara in his homeland before joining Porto in a £2m deal in the summer.