The first derby since the mid-1950s to be played with Dundee in a higher division than their neighbours left a tread more consistent with modern times. Dundee United exited the park with the cheers of their fans ringing in their ears.
The lower league side with no recognised striker made the breakthrough when Paul McMullan, a winger forced to play through the middle, squeezed in the opener on the stroke of half-time.
But Dundee asserted more authority after the interval and Mark O’Hara’s equaliser on the hour mark meant the matter of deciding group winners, top seeds and also city bragging rights came down to a penalty shootout.
New Dundee winger Rorie Deacon, the home side’s top performer in the preceding 90 minutes, missed the decisive penalty, with Harry Lewis diving to his right to save.
McMullan, Billy King, Lewis Toshney and Scott McDonald successfully converted for United, for whom teenager Logan Chalmers missed. Faissal El Bakhtaoui as well as Deacon missed for Dundee, with Randy Wolters, Sofien Moussa and skipper Darren O’Dea scoring.
It is only the second time in this fixture’s history that such a method of separating teams has been required. Dundee United avenged a 1996 defeat in the same competition.
But thanks to a quirk of fate, Dundee have a quick opportunity to make up for a result that felt like a defeat. This being Scottish football, there was no mechanism to prevent two teams from the same group meeting again in the next round. So the Dundee sides will lock horns again at Dens Park a week on Wednesday.
This last 16 re-match seemed to render 90 minutes of toil and sweat, plus the test of nerve that is penalties, redundant. The teams will have to go through another 90 minutes – at least – again, though in sudden-death circumstances this time. There will be no second chance next midweek.
But both teams will feel better equipped for the task after having had another game under their belts. Even so early in the season, United’s resources were tested by injuries. Matty Smith, the teenage striker expected to lead the line in the absence of others, dropped out.
Scott McDonald was introduced perhaps sooner than he – and United – might have wished after 68 minutes to try to inject impetus back into the away side. But honours finished even in the 90 minutes at least, which seemed fair on the balance of play.
Dundee United weathered an early storm – literally as well as metaphorically, a heavy rain shower providing the turf with a pleasing sheen. But the visitors gradually tapped into the force field constructed here over the years by far more talented teams in tangerine jerseys. Ray McKinnon’s new-look side became a very current nuisance to a Dundee side lacking cutting edge.
McMullan put the visitors ahead on the stroke of half-time, shortly after United sent a warning shot across Dundee’s bows when hitting the post through a sharply-hit Billy King shot. United were throwing off the mantle of underdogs, such an unusual guise for them in these cross-street clashes.
Although they kept possession well, Dundee’s first-half threat was restricted to two flashing headers by O’Hara. While they’d created precious little danger, the hosts probably felt confident they would reach half-time still level.
But United were not content with this, Sam Stanton’s shot-cum-cross turned in at the far post by McMullan after Kevin Holt had played both players onside.
It meant the away fans could enjoy a half-time break goading the Dundee fans, something they were always likely to relish given the way things ended for them on their last visit here, when United relinquished their top-flight status.
The visitors were seeking to exorcise some demons. A ground where they had celebrated such notable successes became a theatre of cruelty just 14 months ago. While this event was understandably referenced on more than one occasion by Dundee fans, they were beginning to fret about the task in hand.
But there was still plenty of time to go when a sweeping move, a rarity on such a high-tempo occasion, led to Dundee’s equaliser. Deacon switched the play with a well-directed pass with the outside of his foot to Scott Allan, who picked out O’Hara on the edge of the six-yard box. He was in the right place at the right time to divert the ball past Lewis.
The goal gave Dundee fresh impetus and Holt and Deacon had shots well saved by Lewis, who, at just 19 years old, enjoyed a fine afternoon.
Dundee had two last chances to win the game outright. First Deacon powered into the box. Lewis stood up well again. Then Dundee substitute Jack Hendry, on for the cramp-stricken Kerr Waddell, rose to meet a Holt corner in the dying moments but saw his header bash off the base of the post.