The pensive shot of the Brazilian F1 great was captured by sports photographer Chris Smith during a practice session of the British Grand Prix in 1991.
It is one of a number of Smith's photos up for sale at Chiswick Auctions on May 16, with Smith's snap of Muhammad Ali and the Beatles expected to attract a bid of more than $6,000.
Senna, who died the day after crashing at the 1994 San Marino Grand Prix, finished fourth that day at Silverstone on his way to a third and what would be final championship title.
Considered by many the greatest racing driver of all time, Senna's death has been deeply mourned by millions of adoring fans, notably in his native Brazil.
"Ayrton represents a valuable asset to the country, a bright power for Brazil," Senna's sister Viviane told CNN in 2017.
The Ayrton Senna Foundation in Sao Paulo, managed by Viviane, has helped raise millions for the education of children in Brazil.
'Influential and pivotal'
Smith has 30 years of experience capturing some of the world's legendary athletes at major sporting events.
He first covered the Munich Olympics in 1972 and has since been present at football and rugby World Cups, as well as extensively covering cricket, sailing, horse racing, and boxing.
His photograph of Ali and the Beatles, taken in Miami Beach in 1964, is expected to sell for up to $6,500, with the only other print of this kind in the boxer's hometown of Louisville, Kentucky.
The second photo, also from Miami, depicts Ali as he prepares for the first of his three fights against Joe Frazier in 1971 with trainer Angelo Dundee, who wears Ali's famous slogan "float like a butterfly, sting like a bee" on his back. This is anticipated to sell for close to $4,000.
"We are so pleased to be able to offer works by Chris Smith in our upcoming sale," said Austin Farahar, head of Chiswick Auctions Photographica department.
"He is one of the most influential and pivotal figures in the field of sports photography. His iconic images have a narrative depth that captures not only the skill and strength of athletes, but also captures what drives them to succeed and the psychological characteristics that they possess."
The final photo that completes Smith's auction collection in Chiswick is from the steeplechase during the Hennessy Gold Cup at Newbury race course.
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