Wilkinson, who has no regrets over his decision to retire from England duty, sees a number of parallels between Stuart Lancaster's current side and the team built by Sir Clive Woodward.
England open their autumn campaign against Fiji on November 10 before tackling Australia, South Africa and New Zealand on successive Saturdays at Twickenham.
It is a daunting task but Wilkinson was impressed by the resolve England showed on the summer tour of South Africa, not least in bouncing back from two defeats to draw the third Test.
That achievement sparked memories of England's effort against the Springboks in 2000, when a drawn Test series in South Africa was seen as the launchpad for the World Cup triumph three years later.
"I see England in a great place," Wilkinson said.
"This autumn is crucial. Expectation levels are key. Within the team it should be that we're looking to nail all four. That can start the ball rolling.
"I believe England can beat these teams. There are signs of toughness there now, as we saw in South Africa in the summer. If you manage to do that now, you're in 2003 territory.
"What England need to offer to these big teams when they arrive in the autumn is the message that they can keep battering away but it's not going to happen."
When it comes to the mental toughness required to succeed, Wilkinson sees a great deal of himself in the 21-year-old Saracens and England fly-half Owen Farrell.
"What I do see is that kind of constant battle going on, the sort of inner aggression that comes from battling with yourself," Wilkinson said.
"It is about setting the bar ahead of what the team wants from him.
"For me, that battle fell in the zone between what the team needed and what I wanted.
"My team-mates might be saying that I should be pleased but I was sat in the dressing room mulling over everything. I see a bit of that in Owen.
"That is something for him to harness because it becomes a power that gives you a massive advantage over other people."
After playing in four World Cups, Wilkinson has reconciled himself to the fact he will be a spectator when England host the 2015 tournament.
But Wilkinson retains strong connections with the tournament and on Wednesday he visited the grave of William Webb Ellis. The man reputed to have invented rugby, who the World Cup trophy is named after, is buried in the picturesque French town of Menton.
However, Wilkinson's international ambitions are not entirely on hold and he would jump at the chance to settle some unfinished business with the British and Irish Lions.
Wilkinson was part of the Lions side beaten by Australia in 2001 and torn apart by New Zealand four years later.
"There's no way I could say no. In terms of what that represents, everything about it, it's enormous. Such a fabulous thing," Wilkinson said.
"It is niggling away at me (that I haven't won a series with the Lions)."
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