Scotland continue their World Cup preparations with friendlies against Japan on Saturday and Ivory Coast next Tuesday.
They then host Curacao on 30 May before heading to the USA, where they will be in a group with Brazil, Haiti and Morocco, with the top two plus eight of the best third-placed teams from the 12 groups qualifying for the last 32.
Sir Kenny, who played at three World Cups, believes Scotland have to fancy their chances of getting through to the knockout phase for the first time.
“They’ve done fantastically well to get to the World Cup, it’s a great achievement,” he said.
“There’s three chances of qualification, so three out of four, surely we can get one, hopefully we can get one.”
Sir Kenny was impressed with the 4-2 win over Denmark that clinched qualification.
“They’ve done a fantastic job to get there,” he added. “The game against Denmark was outstanding.
“I don’t think there’s any doubt about the progress they’ve made, even if they don’t do well in the World Cup.”
