McClaren will be back at Wembley on Saturday, leading Derby County in their Championship play-off final against Queens Park Rangers, with not only a spot in the Premier League on the line but a chance to exorcise ghosts of the past.
The 53-year-old endured a forgettable tenure as manager of England after replacing Sven Goran Eriksson, with the nation failing to qualify for the 2008 European Championships.
McLaren's one-year spell at the helm, the shortest period of any England manager, was summed up by the 3-2 defeat to Croatia at Wembley in November 2007, which resulted in him being dubbed the 'Wally with the Brolly' when he sheltered from the pouring rain under an umbrella.
Ahead of his return to England's iconic stadium, McClaren concedes the national team hotseat was too big for him at the time.
"At the time I thought I was ready but the job finds out that you're not ready," he said.
"I didn't have the experience and, together with a little bit of bad luck as well along the way, it didn't work out."
McLaren added: "The biggest thing that hurt me that night, and ever since, was the failure to qualify. That is the biggest thing. It was nothing about anything else.
"As I said on the night, it felt like I'd let the nation down.
"That's what I've had to live with. That's the hardest thing. Nothing else – like 'The Wally with the Brolly.'
"The disappointment will not go away and that still hurts, but you have to get on with life and football."
The former Manchester United assistant has gone a long way to rebuild his reputation, guiding Twente to the Eredivisie title in 2010, while he also went on to coach Wolfsburg in the Bundesliga.
And he could cap a remarkable turn in fortunes if he delivered top-flight football to Derby, though he says his team are the underdogs for Saturday's blockbuster against big-spending QPR.
"There's a lot of pressure on QPR," said McClaren, who was Jim Smith's right-hand man as Derby reached the Premier League in 1995-96.
"It's a necessity they go up really and I know that from being there. QPR's time is now.
"When we came in the door here, we said we had two-and-a-half or three years to get Derby back into the Premier League.
"We will have our opportunity again if we don't take it now."
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