There was derby delight for Dundee United at Dens as they first drew with Dundee then earned the bonus point thanks to a 4-3 penalty shoot-out success.
The visitors had taken a deserved lead in the final minute of the first half through Paul McMullan but Mark O’Hara levelled for the Dark Blues on the hour.
With no further scoring, the shootout was required to decide which club would get the bonus point and top Betfred Cup Group C, with both sides already through to the next round.
McMullan was first up for United and scored, with Faissal El Bakhtaoui having his kick saved by Tannadice goalie Harry Lewis.
Billy King, after a delay, slammed the ball home before sub Randy Wolters got the hosts off the mark.
United’s Lewis Toshney made it 3-1 before Sofien Moussa found the net for the Dens men.
Young Logan Chalmers then had his kick saved by Dark Blues goalie Scott Bain before Darren O’Dea made it 3-3.
Sub Scott McDonald found the net for United to edge them ahead only for Roarie Deacon’s effort to be saved by Lewis.
That sent Ray McKinnon’s men through as group winners with 11 points to their opponents’ 10.
The Dark Blues, as expected, were unchanged from the side that started the comfortable 3-0 victory over Cowdebeath. The fit-again El Bakhtaoui was on the bench.
The Tangerines, meanwhile, had to deal with their selection problem, particularly up front. Without Patrick N’Koyi and James Keatings through injury and latest signing McDonald lacking match fitness, manager McKinnon had been expected to keep young Matty Smith up front.
However, McKinnon pushed McMullan into attack and Smith dropped down to the bench along with Jamie Robson. Mark Durnan came back to central defence and Scott Allardice slotted into the midfield, while there were substitute spots for both McDonald and Willo Flood.
The home side got the action under way and there were some early jeers from the United end for former Tannadice playmaker Scott Allan, now wearing blue and white.
The visitors had the first decent chance on five minutes, with Scott Fraser playing the ball on to Sam Stanton, who pulled his shot wide of Bain’s goal.
Dundee were winning a few freekicks and there was anxiety in the United box on seven minutes when Allan swung one into the goalmouth that had to be scrambled away. From the resultant corner sent over by Kevin Holt, O’Hara got his head on the ball at the back post but visiting keeper Harry Lewis was well positioned to save.
The home team had enjoyed the better of the early possession but United had a great chance from a freekick on 13 minutes after McMullan was fouled just outside the box by Allan. Fraser took the kick but it merely sailed into Bain’s arms.
With 20 minutes gone, the heavens opened and down came the rain to absolute soak the players and, more importantly, the pitch. That would be a test for both teams but it relented a bit after 10 minutes or so.
McMullan swung over a freekick for the Tangerines that missed Bain’s bar by a foot or so then, on 31 minutes up at the other end, O’Hara glanced a header goalwards from Holt’s cross but Lewis did well to make the stop.
Just a minute later, United came within a whisker of making it 1-0.
They took a freekick in the middle of the park that eventually found its way to Billy King, who ran on before smashing his shot against Bain’s right-hand post, with the goalie beaten.
Home captain O’Dea was booked for tripping McMullan and King fancied his chances from the freekick, which was just outside the box. This time, though, Bain palmed away his swerving strike.
It was United who were now enjoying more of the ball and they took a dramatic lead in the final minute of the first half.
They were troubling the Dark Blues with their quick, accurate passing and that was what gave them the lead.
They broke up the left then then swept into the box via Stanton, who looked like he might be the scorer. However, the ball made its way to the back post and McMullan deftly steered it back across Bain, who had moved across the six-yard box to try to block.
It was a lovely finish from McMullan and the Tangerines walked off with a spring in their step.
McMullan’s next involvement was a booking on 51 minutes for a foul on Cammy Kerr right in front of the home dugout before King pulled a shot wide after yet more good attacking play from McMullan.
The Dens men had the ball in the net on 55 minutes when Moussa headed home but the big Tunisian was well offside and it was no surprise when the flag went up. Moussa then tried an overhead kick that was easily saved by Lewis.
The home side were looking threatening now and they got the equaliser bang on the hour mark.
It was a well-worked goal, with Allan crossing from the left to O’Hara, who played the ball down into the ground and then up beyond the reach of Lewis.
The United goalie beat away a cross from Deacon as the match swung towards the Dark Blues before saving a vicious strike from Holt.
The Tannadice men brought on McDonald for Fraser on 68 minutes, while El Bakhtaoui replaced scorer O’Hara for the hosts.
El Bakhtaoui tested Lewis with a shot from distance that the United goalie did well to smother.
United brought Flood off the bench to replace Allardice, while Wolters came on for Allan and Jack Hendry replaced an injured Kerr Waddell for the home side.
Flood’s name was in the ref’s book for a foul on Kerr before the Dens men squandered three golden chances in injury time to take the three points.
Firstly, good work from Paul McGowan set up Deacon but Lewis came out to make a brilliant block then a header from sub Hendry struck the inside of the United post. Next up, El Baktoui’s net-bound strike was cleared.
Those escapes for the visitors took the tie to the decider, which they stayed cool long enough to win.
Attendance: 10,460.
Dundee: Bain, Kerr, Holt, O’Dea, Kamara, Moussa, Allan (Wolters 78), O’Hara (El Bakhtaoui 70), McGowan, Deacon, Waddle (Hendry 80). Subs not used: Parish, Vincent, Haber.
Dundee United: Lewis, Scobbie, Durnan, Toshney, McMullan, Fraser (McDonald 68), King, Stanton (Chalmers 90), Edjenguele, Allardice (Flood 77), Briels. Subs not used: Deniz, Donaldson, Robson, Ballantine.
Referee: Kevin Clancy.
