Glasgow Rangers' recent victory over Dutch opposition qualified them for the lucrative group stage of the Champions League for the first time since the 2010/11 season.

With the Ibrox side expected to receive up to £30m in prize money for qualifying, it would have been expected that Giovanni van Bronckhorst could have used some of this to further strengthen his squad before the transfer window slammed shut.

It didn’t quite work out like that, and with the 4-0 hammering from Premiership arch-rivals Celtic at the weekend, the decision is looking rather foolish.

Times have changed in Scotland - no longer can the Old Firm routinely spend £8m-£10m on players anymore. Since Tore Andre Flo made his landmark move to Rangers in November 2000 for a fee of £12m, the only time that the Light Blues have ventured over the £7m mark is when Ryan Kent joined from Liverpool in 2019 for a total fee of £7.5m.

The landscape could well have been changed once and for all in 2000 when then-Rangers manager Dick Advocaat tried to sign Ruud van Nistelrooy from PSV Eindhoven, the team who Van Bronckhorst's current crop defeated in the Champions League play-offs a fortnight ago.

It’s a story which defies belief now, but at the turn of the century, the Gers were spending outside their means, and it wouldn’t be until 2012 that this frivolity caught up with them.

Advocaat tabled a £15m bid for the striker, who was in high demand following his spell at PSV, scoring a remarkable 77 goals in just 90 appearances.

A move to Rangers would have made waves across the continent and surely would have improved the Light Blues' dismal European record at the time, failing to qualify from the group stages of the Champions League in both 1999/2000 and 2000/01 despite the sheer quality of the squad.

Sir Alex Ferguson stepped in and eventually sign the prolific Van Nistelrooy for Manchester United, completing a then-British record transfer of £19m, and he had a tremendous spell at Old Trafford.

Fergie dubbed him “fantastic” when the Dutchman broke Denis Law’s European goal record for the club in September 2004, and its fair to say that the move was a success, netting 150 times in 219 Red Devils appearances.

It was a massive what-could-have-been for Rangers. If they had managed to convince the superstar to swap Eindhoven for Glasgow 22 years ago, one can only imagine how many goals he would have scored against the likes of Aberdeen and Celtic, rocking the crowd at Ibrox time and again.