An injury-time defensive calamity handed Dundee a place in the last 16 of the Scottish Cup, with Drey Wright's simple finish extending nine-man Kilmarnock's winless run to 16 matches.

New Rugby Park signing Kelle Roos rose to catch a simple ball late on, but was challenged by his own defender Robbie Deas and the ball fell perfectly to Wright to complete a comeback for the visitors.

Kilmarnock took an early lead through a stunning Dominic Thompson volley which struck both posts before settling in the net, but from there were largely on the backfoot against a side intent on attack.

Ashley Hay had already gone close on a couple of occasions and his persistence paid off when he drove in a leveller.

A second yellow card for Jack Thomson tipped the balance in Dundee's favour before Wright's winner, further compounded by a second red card for Lewis Mayo for illegally ending a Dundee counter with Roos stranded upfield.

Kilmarnock failed to end their barren run of results in new manager Neil McCann's first home fixture in charge, with their last win coming at the start of October.

Kilmarnock got the crucial advantage early on but it felt, at that stage, against the run of play. Their goal was a thing of beauty from Thompson, though.

It wasn't too long ago that he was remonstrating with home fans after a home defeat by Falkirk. His opener was the polar opposite. An unbridled moment of joy for all concerned with Kilmarnock, something that's been rare of late.

But McCann's side just couldn't stem Dundee's determination to attack. They showed fight and defended doggedly but struggled to find a balance to trouble their visitors too often.

It's 16 games without a win now and an exit from the Scottish Cup. The manner of losing this will compound the outcome. Clearly there was no communication. It was really, really poor from Roos and Deas to gift Dundee the win.

The run they are on needs arresting as soon as possible but confidence will take a hit from that moment alone.

Dundee merited progression from this display. Their attacking intent was relentless with the woodwork and some inaccurate finishing undermining their performance.

They did so many things well, throughout, outside spotting Thompson's late run for Kilmarnock's goal.

They responded to that setback and took the game to their opponents. That final finish marginally evaded them but on another day they surely would have earned victory more comfortably than they did.

Pressley's side look a decent outfit on recent evidence.

Out wide Yogane look a real threat and his trickery and pace cost Thomson a red card. A lot of positives for Dundee fans to enjoy.

Kilmarnock manager Neil McCann: "When we go down to ten men, it's going to be difficult.

"I'm so disappointed for the fans and the players who put so much into it. I thought we defended very well, but that mistake at the end, there is just one of those moments you need to suck up and take.

"I was just a lack of communication, Kelle's just in the door, I thought he was terrific in the match, he looked solid in goals, he did what we asked him to do, but maybe it was just a bit of communication in the message.

"You need to be decisive in that moment; it's a real killer in the dressing room.

Dundee manager Steven Pressley: "It was always going to be difficult coming here with the bounce of a new management team. We found ourselves behind at half-time after a very good first-half performance.

"I've told the players we have to prove ourselves over a long period of time. I'm really pleased that we've progressed through to the next stage. It's a great competition. We don't want to be at home watching other teams in the next round.

"I've got to say it was a really difficult game against a very organised Kilmarnock side, they kept us at bay for large parts of the game, but we showed that bravery and mentality that I think is growing within the team."

Kilmarnock face a stern test when they travel to face Motherwell on Saturday January 24th (15:00 GMT) as they look to climb the Premiership table.

Dundee face a trip to take on rejuvenated Rangers at Ibrox the following day (15:00).