Frustration reigned at the Excelsior Stadium for Dundee and manager Tony Docherty as he saw his side fall to a 1-0 defeat to Airdrieonians.
The reverse, thanks to a late Rhys McCabe penalty, puts the pressure on the Dark Blues in their bid to progress from Viaplay Cup Group E.
Dundee had the opportunity to take the lead from the spot themselves earlier on in the second half after Scott Tiffoney was taken down by Josh Rae.
However, Lyall Cameron’s effort from 12 yards was turned around the post by the Diamonds goalie.
‘Why it is a penalty I don’t know’
Docherty, though, was not happy with the decision from referee Colin Steven.
“I don’t think it’s a penalty kick. I don’t think there’s enough contact the referee is really quick to make the decision,” the Dundee boss said.
“I’m really disappointed with that but more disappointed with the team performance because we should have had the game won by then.
“I’m disappointed we missed our penalty. Zach Robinson is our normal penalty taker but young Lyall took the responsibility, he was confident enough to go and do that.
“Fair play but when you get that opportunity you need to score.
“When you aren’t clinical in front of goal, you allow those situations to happen. Ultimately that’s what’s done us today.”
He added: “I feel for young Jack (Wilkie) as the decision went against him and I am disappointed for him.
“Why it is a penalty I don’t know and it is a harsh lesson for him as we lost the tie.
“As a team we have to take responsibility for that as when we were dominant we need to convert that into goals and points.
“We didn’t do that.”
Antonio Portales and injuries
That was on the pitch, off it the frustration continued for the Dundee boss.
Missing the trip to Airdrie were key players Zach Robinson and Owen Beck after picking up knocks in training.
New Mexican striker Diego Pineda was available after joining the team for training on Thursday, replacing Zak Rudden on 59 minutes.
However, compatriot Antonio Portales will have to wait for his debut due to an error from the Mexico Football Federation.
“I am frustrated we didn’t have Antonio here,” Docherty added.
“The Mexican federation made a mistake on when he was out of contract with his club.
“The result came through that Diego could play and he did well.
“We’re hoping Antonio will be ready for Wednesday (against Dumbarton).”
“It’s been frustrating as we want our best players on the park.
“We had Zach Robinson and Owen Beck missing and they are good attacking options for us. They should be fine for Wednesday hopefully.
“I thought with the team we selected we should have had enough to win the game. We weren’t troubled too much.
“On reflection we should have won the game easily and it is a huge disappointment.
“But we need to dust ourselves down and get ready for the next game because it’s more important.”
The defeat leaves Dundee in fourth place in Group E, three points behind leaders Airdrieonians and two behind Wednesday’s opponents Dumbarton.