Striker Freedman knows what to expect Saturday having previously played twice against the Londoners.
In January 2000 he was part of a Nottingham Forest side which lost 2-0 at Stamford Bridge and five years later he came on as a substitute as Crystal Palace suffered a 4-1 defeat at the same venue.
Speaking to the Southend Evening Echo Dougie said: "You just how to approach it like you would any other game. You need to do what you would normally do for a league game and eat the same pre-match meal, do the same warm up and just do everything exactly the same. It's obviously easier said than done when you're about to play a team like Chelsea but that's the main piece of advice I will be giving to the younger players in the team. They also have to make sure they enjoy it. I've played at Chelsea before and it's a great place to go and test yourself. The club has grown massively over the last 15 years or so because when I first came to England from Glasgow I joined QPR and at that time they were of a similar size to Chelsea. The league positions and crowds were virtually the same but now Chelsea are one of the biggest clubs in the world."
34-year-old Freedman, four goals in seven games for his latest club, has wracked up more than 550 appearances during his long career, making him the perfect man to help out the younger players on how to handle such a big occasion.
He knows the current Chelsea side will not take Southend lightly: "They wouldn't have got to a club like Chelsea if they did but we need to work as hard as we can and give it our best shot. When the game starts we aren't going to suddenly become the best team in the world but we want to give a good account of ourselves."