The 37-year-old spent eight years with the Scottish Championship leaders.
The 37-year-old was appointed as the Premiership side's temporary boss following the resignation of Gary Locke in the wake of the club's 1-0 home defeat to Hamilton on Saturday (via Record). And with his first test seeing him come up against Mark Warburton's men in the Scottish Cup, McCulloch reflected on the prospect of returning to familiar surroundings.
He told the Record: "It's pretty surreal, isn't it?
"I'm looking forward to going back to be honest. I had eight great years there, no regrets. If you're not wanting to go and play in this game then you shouldn't be in football."
In terms of places he would have selected to make his managerial debut, the ground he called home for eight years would have most probably been right up there. The former Wigan man experienced both extreme ends of the spectrum during his time with the club, winning three Premiership titles, but also having to help the Gers begin their journey through the divisions after their demotion.
And while his loyalties will surely lie with his current club on Saturday, he will be desperately hoping that - with Killie fighting for survival in the top tier, while Rangers close in on the Championship title - their next meeting comes next season and is a Premiership fixture.