Mark Warburton's Glasgow Rangers side were surprised by Hibernian at Hampden Park.
Rangers' Kenny Miller
Despite the disappointment that came from the Gers losing 3-2 to Hibernian in dramatic fashion, Miller made the trip into the winners' dressing room immediately after the game, and he explained that although it was difficult to accept the result, he was over the moon for McGregor, who spent the previous campaign at Ibrox.
Darren McGregor during his season with Rangers
"I know a few lads in that team - I went along to see big Daz [Darren McGregor]. As much as I was really, really disappointed I was delighted for him," he told the Evening Times.
"He was a great lad at this club, did a really good job for us over that year and for one reason or another he had to move on and got a great move back to the club he supported as a boy."
Though the defeat - and the nature of it - would have been a difficult pill to swallow, the loss may ultimatey be looked back upon as an important lesson for Mark Warburton's team.
After wrapping up the Scottish Championship title and beating their Old Firm rivals, the Gers endured their worst spell of form since Warburton arrived the previous summer.
But had they won the clash with Alan Stubbs' men, they may have been more tempted to sweep some of the problems under the carpet, which would have had a negative impact on the side's fortunes back in the top flight with the standard of opposition stepping up a level.
However, the loss confirmed that there were still issues to address, and may have been the catalyst behind Warburton's decision to make eight new signings before their first game of pre-season.