The Brazilian lost out to Hamilton by a single point in one of the most dramatic finales in the championship’s history.
And while the outcome of that season-ending Brazilian Grand Prix is beyond reproach, serious questions remain about that year’s Singapore Grand Prix.
There, Nelson Piquet Jnr was instructed by the senior management of the Renault team to crash his car to help team-mate Fernando Alonso.
Massa finished outside of the points in Singapore after a refuelling issue, while Hamilton was third.
The conspiracy surrounding that event was made public by Piquet in 2009.
Last year, Massa revealed that he was considering legal action over how the ‘crashgate’ controversy was managed.
His action came following comments from Formula 1’s former commercial tzar, Bernie Ecclestone, who admitted he knew about the scandal well before it became public – and in time to have acted before the end of the 2008 championship.
It’s also claimed the late Max Mosley, then president of the FIA, was also aware of the controversy.
Once the incident became public knowledge, Renault’s Pat Symonds (technical director) and Flavio Briatore (team principal) were handed lifetime bans.
Those were overturned by a French court, with both now working as consultants with Formula 1.
Regardless of the proven wrongdoing by Renault, the result has remained, and Alonso remains the official winner of the 2008 Singapore Grand Prix.
Initially, Massa’s legal plight intended to overturn the outcome of that year’s world championship.
Should the Singapore Grand Prix result be annulled, the Brazilian would be the world champion.
It’s believed overturning the world championship result is impossible once the FIA prize-giving ceremony has been held.
As such, Massa is pursuing £64 million (AUD $124 million) in compensation for what he deems a loss of income due to not winning the title.
Documents filed to the London High Court claim that Massa missed out on a €2 million bonus from Ferrari by not winning the championship, on top of potential salary demands he could have made in subsequent years.
Combined, it estimates his loss to be £64 million.
On top of chasing financial compensation, Massa is also seeking acknowledgement from the FIA that it failed to follow its own rules as laid in the International Sporting Code.
Massa argues that, given there was knowledge of the incident before the conclusion of the 2008 prize-giving ceremony, and that no investigation was carried out, the sport is in breach of its own rules.
He’s therefore instigated legal action in the London High Court against the FIA, Formula One Management, and Ecclestone.