Ross County snapped Dundee’s 10-game unbeaten run with a 2-0 win in Dingwall.
Tony Docherty’s side had not lost in any competition since the tail end of last season, but Akil Wright’s sixth-minute header and Jordan White’s penalty in first-half stoppage time gave the Staggies a strong advantage.
Try as they might after the restart, Dundee could not find a route to goal which meant that the points stayed in the Highlands.
Playing with the wind at their backs in the first half, it was hosts County who made the faster start.
White went close just a few minutes into the match, with his effort going just the wrong side of the post after a cross from the right wing was not cleared, and minutes later the Staggies went ahead.
Noah Chilvers’ corner was met by Wright at the back post, with the defender rising highest to head into the net.
It was not completely plain-sailing for County, as George Harmon was forced off with injury after trying to run off an early issue.
Dundee did look to grow into the contest as the half wore on, and Simon Murray thought he had equalised against his former club after meeting Billy Koumetio’s excellent pass through the middle of the pitch.
But although he beat Ross Laidlaw to find the corner of the net, the offside flag was raised at the sidelines – a decision quickly backed up by the video assistant referee.
VAR would get involved again right at the end of the half, with a seemingly innocuous corner awarded to County instead being turned into a penalty when Ethan Ingram was judged to have pulled down White.
White stepped up himself to convert to send the Staggies into half-time with a 2-0 lead.
Although Dundee came out for the second half determined to get back into the contest, they struggled to properly test Ross Laidlaw.
There were two moments when they claimed they should have had a penalty – the first saw Ziyad Larkeche booked for diving, and the second on Murray saw no action taken even after a VAR check.
However, County staunchly defended their goal and managed to keep their visitors at bay to record their second league clean sheet of the campaign and claim all three points.