The Scots currently sit third in Group I, behind Czech Republic and Spain, and need at least four points from their final two outings.
Saturday sees Caldwell and his teammates take on Liechtenstein in Vaduz before traveling to Alicante for a crack at World Champions Spain and the 29-year old is full of confidence.
"We would rather have qualified before going to Spain and we could maybe have enjoyed it a bit more. But it is what it is," said Caldwell.
"Hopefully we find ourselves in the position where we are a point clear going into the Spain game and we can go there and try to beat the best team in the world.
"I think it would sum Scotland up that we go and do that to finally qualify. Everybody is looking forward to that challenge.
"You look at France a few years ago when we went there and won and they were a tremendous team.
"We can do it, we have done it in the past. We always seem to raise our game for the big nations and hopefully it can be a great night. But we have a big job to do on Saturday before we can look forward to that game."