The former Coventry City manager described the Wanderers as the form team in Britain at the moment and admits his players have to be at their best if they are to progress through to the final stages of the competition.
"Bolton are the form team in Britain at the moment. Every time we play them it is close, we have drawn the last two league matches down here and up there" he said.
Strachan also pointed out that even during a cup tie in November 2001 there was very little to separate the Trotters from their South Coast opponents. Former Southampton forward Rod Wallace scored the winning penalty for Bolton that night in what was 120 minutes of even football.
"Even the league cup tie was a draw after extra time and five penalties each, i'm sure it will be a close game again and maybe even spot kicks. You cannot practise for a penalty shoot out though. You can take as many as you want on the training ground but it is completely different"
"You cannot prepare for the pressure of the situation. It is one thing sticking them away in training but can you do it in front of 25,000 people willing you to miss?, that is very difficult."
The former Manchester United and Leeds midfielder is aware of the prize at stake and is hopeful that the Saints can get to their second final in a year having reached the FA Cup Final last season when they lost out to Arsenal at the Millenium Stadium in Cardiff.
"Hopefully we can win in open play but we know how hard it will be because Bolton are flying right now. There is a huge prize at stake though with the prospect of another Semi-Final. We had a taste of it in last year's FA Cup and of course we would love to go back to Cardiff"