In November 1998, just four months after joining Rangers from Feyenoord, the competition brought him his first winners’ medal with the Ibrox club when they defeated St Johnstone 2-1 in the final at Celtic Park.
But while it is a tournament which has given Rangers and their supporters many memorable occasions through the years, winning it a record 27 times, addressing their more miserable recent history in it is the first item in new manager van Bronckhorst’s in-tray which has to be addressed.
The Dutchman will have a watching brief from the Hampden stand on Sunday afternoon as he awaits the work permit which will allow him to formally take charge of his new squad from the technical area.
The semi-final showdown with Hibs, however, is still very much the start of van Bronckhorst’s tenure as he succeeds Steven Gerrard.
Rangers have not won the League Cup since the 2010-11 season and despite the considerable progress made by the club on Gerrard’s watch, he was unable to improve their domestic cup woes.
A solitary League Cup Final two seasons ago, when Rangers lost 1-0 to Celtic at Hampden, was the best Gerrard could muster.
If van Bronckhorst can bring the famous three-handled trophy back to the Ibrox trophy room before the end of the year - the final is on December 19 - it would be a propitious start to his time in the role.
But although Rangers are odds-on favourites to overcome Hibs this weekend, the Easter Road club enjoy something of a hex over them at this stage of the League Cup.
In their five previous semi-final meetings, Rangers' only victory came in the first of them in the tournament’s inaugural season of 1946-47.
Hibs have prevailed in each of the subsequent four last-four ties between the clubs - in 1972-73, 1985-86, 1991-92 and, most recently, a penalty shoot-out triumph in 2003-04.
Remarkably, it’s 42 years since Rangers beat Hibs in any competition at the national stadium when they eventually emerged successfully from the twice-replayed Scottish Cup Final of 1979.
With van Bronckhorst restricted to a view from the posh seats on Sunday, directing matters from the side of the pitch will fall to the four-man coaching team of B team manager David McCallum, his assistant Brian Gilmour, veteran player-coach Jermain Defoe and goalkeeping coach Colin Stewart who have overseen the preparations while Rangers concluded a deal for their new manager.
Among the selection decisions to be made is whether Alfredo Morelos returns to the starting line-up. The Colombian striker was an unused substitute in what proved to be Gerrard’s last match in charge, the 4-2 league win against Ross County at Ibrox a fortnight ago.
Fashion Sakala, who scored four times in his two outings for Zambia during the international break, is making a strong claim to lead the line.
Winger Ryan Kent, who scored and shone for an hour against County in his first start since returning from injury, is likely to be a key figure for Rangers again as they look to seize the attacking initiative and put on a show for their new boss.