"Always the bridesmaid," she said then.
Not any more.
Grainger finally climbed atop an Olympic podium on Friday, and this time she was crying tears of joy.
"I'm a bride at last," she exclaimed Friday, draped in a Union Jack flag on another golden, emotion-filled day for British rowing. "I'm going to go round the country with my gold medal until people are sick of the sight of me."
That'll likely never be the case.
Grainger was already a popular figure — the Steve Redgrave of female rowing in Britain — before she completed her 12-year quest for Olympic gold by winning the double sculls with Anna Watkins at Dorney Lake.
Given her past near-misses at the Olympics, the triumph of the 36-year-old Grainger will be celebrated long and hard in the host nation.
The roar she and Watkins received from the 30,000-strong crowd as they closed in on the finish line was as deafening as anything heard in the first seven days of the Olympic regatta.
"I feel this medal, of all of them, is the people's medal," Grainger said. "I feel so many people have been behind me and supported me and wanted this for me as much as I have.
"Every single person's been a part of this and it makes the medal seem so much more special."
Redgrave, a winner of rowing gold at every Olympics from 1984 to 2000, was there for her big moment. He was standing on the jetty as Grainger clambered out of her boat and they embraced warmly.
She then turned around and waved to the grandstands. It was only when "God Save the Queen" rang out during the medal ceremony that the first tears fell.
"On the podium, we knew how special it was," she said. "We knew it at that moment and that moment is everything you hoped it would be."
Grainger was runner-up at the 2000 Olympics in the quadruple sculls, in the '04 Olympics in the pair and in '08 back in the quad.
It was the Beijing silver that hit her hardest. Her crew was a big favourite and the manner of the loss — China produced a late surge to win by a half-length — was tough to take.
Grainger contemplated retirement but was driven on by the thought of ending her Olympic jinx at a home games.
"As a person and an individual, I would still have been a happy secure person," she said. "But as an athlete, I would have felt I'd underperformed."
Her pairing with Watkins came about by chance, at a random training session in 2010, but it felt good straightaway.
They have never come close to losing and Friday's race was another performance mixed with grace and guts.
Rowing into a strong headwind, Grainger and Watkins bided their time before pulling clear of Australians Kim Crow and Brooke Pratley in the second 500 metres.
With 500 metres to go, they both knew gold was in the bag.
"There was no way anything was going to go wrong," said Watkins. "We had time to enjoy it, which is more than we could have dreamed of."
The Britons won by 2.73 seconds, sparking jubilant scenes among the spectators.
"That is the story of the British medals so far at these games," Redgrave said.
Grainger refused to rule out continuing through to the Rio de Janiero Olympics in 2016, when she will be 40 years old.
"We haven't discussed beyond London," she said. "We were just aware that Aug. 3 was a massive day and the race of our lives. To be honest, we don't even know what we're doing tomorrow."
Before the London Games, a British female had never won Olympic gold in rowing. With Helen Glover and Heather Stanning winning the pair on Wednesday and Kat Copeland and Sophie Hosking favourites for the lightweight women's double sculls on Saturday, the host nation could end up with six female gold-medallists by the end of the regatta.