Former Scotland manager Craig Brown believes there is no better time to take on England than Friday at Wembley.
Brown was in charge when Scotland last won at Wembley in November 1999 thanks to a Don Hutchison header, although England progressed to Euro 2000 with a 2-1 win on aggregate.
England were victorious in the two friendly meetings that followed in 2013 and 2014, with the fixture returning on Friday in a crucial World Cup qualifier.
The qualifying campaign to reach Russia 2018 has got off to a sticky start after a 1-1 draw against Lithuania and a 3-0 loss in Slovakia, while England failed to impress in last month’s double header under caretaker manager Gareth Southgate.
An underwhelming 2-0 win against Malta was followed by a 0-0 draw in Slovenia. Brown believes the turmoil created by former England manager Sam Allardyce’s departure after only one game in charge following a newspaper investigation into football corruption has boosted Scotland’s chances of an unlikely victory.
He said: “I think we’ll win 2-1. I feel strangely optimistic for a number of reasons. The main reason is that Wembley is an inspirational place to play and I think the Scotland players raise their game when they play there.
“I never had a disappointing Scotland performance at Wembley.
“The England team is in a serious period of transition and I think it would have been more difficult for us if the FA had told Gareth Southgate he was the manager.
“He is on trial and I think it would have been more difficult if England had acted promptly.
“England won every game in their last qualifying group but it will be a lot tougher for them this time.”
Scotland will don a fluorescent pink strip for this Friday’s encounter but Brown believes the jersey may bring luck.
The former Aberdeen manager said: “I actually don’t especially like the current home strip which is dark blue with the white sleeves.
“The white sleeves are the reason we have to change and I would rather Scotland played in an all dark blue kit – but I don’t care what they play in as long as they win.
“The best performance I ever had with the Scottish team was when we wore pink in Germany in 1999 when Don Hutchison scored the only goal.
“Not only did we beat them but we played exceptionally well.
“The best player on the park that day was the current manager of Dunfermline Athletic, Allan Johnson, who had a wonderful game. The German full back he was up against got such a torrid time he had to pay to get back in the stadium.
“Ian Durrant also had a very good performance as did Brian O’Neil, a former Aberdeen player.
“Germany had a top team out but we played brilliantly that night.”
The former Scotland manager believes Scott Brown’s decision to step out of international retirement for the fixture can only be beneficial for Gordon Strachan’s side.
He added: “It is good to have a Brown in the Scotland team going to Wembley.
“Bobby Brown was in charge when we won there in 1967 and I was in the dugout when we last won at Wembley in the second leg of the play-offs in 1999.
“Although we lost 2-0 in the first leg I went down there with optimism, I certainly didn’t have any trepidation.
“We have got Scott Brown this time, so that is a boost.
“I was pleased he decided to come back and hopefully he can play a part on Friday.”