Brown led Scotland to victory over the likes of David Beckham, Paul Scholes and Alan Shearer on their last competitive game at the old Wembley Stadium in 1999.
England were two up before the second leg kicked off and Kevin Keegan’s men ultimately qualified for Euro 2000 but the hosts are in a state of flux this time with Gareth Southgate in temporary charge following Sam Allardyce’s brief period at the helm.
Although England sit three points above Scotland at the top of their World Cup qualifying group, their goalless draw with Slovenia has given Brown enough hope that they are there for the taking on Friday night.
Asked what Scotland need to do to emulate his team’s Wembley win, the 76-year-old said: “They have got to be brave and confident and not go down there with any feeling of inferiority, because England are on a wobble at the moment.
“They struggled in the last game they played and even the game they had with Big Sam, they weren’t convincing at all.
“So I think England are in a transitional period and they are not stable.
“I think it gives Scotland a great opportunity because we always rise to the occasion when we go to Wembley and I’m sure we will do that this time.”
Don Hutchison’s goal in 1999 was not enough to overturn a 2-0 first-leg deficit but England were rocked and needed David Seaman’s reflex save to prevent Christian Dailly’s header taking the play-off into extra time.
Scotland had been written off before making the trip to London after Paul Scholes’ double at Hampden had put England firmly in the driving seat.
And Brown feels inner belief was and will be crucial in the oldest international fixture of them all.
“We were two down when we went down there and I emphasised to them that this was a great opportunity to redeem ourselves and get revenge,” said Aberdeen director Brown, who was helping launch the North Lanarkshire Sporting Hall of Fame.
“The revenge aspect was quite important. Even though we were successful, we could have been more successful.
“We were always together even though we were beaten. We weren’t beaten too often, I’ve got to say. We were determined to qualify. We had qualified for the last two tournaments. We got a very difficult opponent. I think anyone else we would have beaten.
“But the motivation was there. We were two down playing the Auld Enemy.
“You want to rewards the fans. I was always conscious of the Tartan Army. In every team-talk, I said, ‘Look, it’s cost these guys a fortune, not just in travel but in drink, to come and support us, so you have got to give them value for money’.
“I always said, ‘you must bust a gut for Scotland’, and on every occasion they did that.”