IT probably was a little unfair to ask Rory McKeown to show us his medals.

He doesn't really have any for one thing, most of his nascent career having been spent in the relatively esoteric environs of youth football. There were a few tournaments as he progressed through the ranks at Ipswich Town and even a couple of finals with boys' clubs in Northern Ireland – the sort that promised little more than a certificate and a photograph in the local paper. To the winner the spoils, then.

Yet his first season at Kilmarnock has proven to be a lot more prosperous. Or, at least, it could. The Ayrshire club have already reached the semi-finals of the Scottish Communities League Cup, where they will face Ayr United at Hampden later this month, and they will add to that an appearance in the fifth round of the William Hill Scottish Cup if they can belatedly negotiate a way past Dundee tonight. Kilmarnock have already had one crack at it and were left to celebrate a replay, the first division side having missed a penalty in a gripping encounter at Dens Park.

If McKeown had anticipated a brusque tie earlier this month then he would prefer to have a far easier time of it tonight. The full-back left Tayside impressed with how Dundee had performed – "The boy [Gavin] Rae used to play for Rangers and is a big player, and I thought the right-back in that game [Gary Irvine] played well" – but not enough to provoke consternation about their arrival at Rugby Park. He retains a youthful enthusiasm towards cup competition, a trait which betrays the mature performances he has offered this season. McKeown will need to rely on both tonight.

"Last year I was playing youth football down in England and then this year I'm playing in the semi-final of a League Cup and playing in another cup [tonight]. It has been a big change but definitely one I've enjoyed," said the 19-year-old. "A good cup run raises our profile and it's a nice feeling too, going and playing in a big game with a lot of coverage. It makes you feel good and makes the fans feel good.

"The semi-final is going to be a big game for everyone, but first and foremost we've got Dundee. They should be an SPL club. Last time they came out, pressed and didn't give us an inch of space. They will be looking to cause an upset and make a bit of a name for themselves, but we are going to go and pass them off the park. That's the plan anyway."

Recognising who he is passing to could be a problem, though. Kilmarnock have been blighted by a number of injuries ahead of the replay, while new signings Ben Gordon and Michael Nelson are both ineligible as they were not signed ahead of the initial tie. The latest head count suggested there were as many as 10 first-team players hobbling around the club and a handful of the under-19s have been promoted to fill the gaps.

Not that you would have guessed any of that from the demeanour of Kenny Shiels. The Kilmarnock manager is an engaging character, if also vulnerable to the odd jibe given his strong principles, and he was at it again yesterday. He would have been forgiven for allowing his depleted side to supplant their usual passing game in a potentially terse match, but Shiels was more concerned about the impact that would have on the younger players that have been drafted in.

"These young lads are being asked to play our way," he said. "We can't change that or we are sending them mixed messages. James Dayton, David Silva and Gary Harkins are all doing tests but if we push them then they will not be ready for Saturday. Which do you salvage? It's a juggling act."

His search for further additions has also taken something of a twist, with Mark Kerr due to begin a trial this morning. The former Aberdeen midfielder spent last week training with Dunfermline Athletic and has arranged a similar spell in England. Shiels also conceded that Derek Riordan is unlikely to join his squad, with the forward reportedly owing a hefty tax bill if he signs for a British club following a brief stint in China. "Because of you-know-what he has to go to Europe, he has to get out of the UK," said Shiels of a player also interesting Blackpool.

Meanwhile Matt Lockwood, the man who missed from the spot in the first match, has revealed he won't be on penalty duty for Dundee this evening, instead standing aside for one of his team-mates – most likely Steven Milne – should his side get one in regulation time. The defender insists, however, he will put himself forward if it goes to a shoot-out.

"We should have won the first game," he said. "If I had scored the penalty we would have gone through 2-1. But this is a clean slate. We can't afford to think of what might have been but we've got another bite at the cherry. We know it's going to be tough as they're a good side but they're not invincible. We know we can do it. We have been doing really well over the last couple of months so we're obviously quietly confident going into the game.

"It's a shame we didn't finish the tie here when we had the chance but these things happen. This is another day. They're at home now so they are favourites but if we go out and play well then we can cause them trouble. That's what we plan to do."