Stallone’s collection, which spans more than 20 years, includes a Panerai Luminor Submersible 1950 PAM00382 – a model that was also worn by Dolph Lundgren, Jason Statham, Terry Crews and Randy Couture in the 2012 action film.
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The Rocky star, 77, said it was “bittersweet” to sell 11 of his timepieces but added that “they serve as a reminder that hard work pays off”.
The auction’s headliner is a Patek Philippe Grandmaster Chime 6300 which is expected to fetch between $2.5 and $5million (£1.99million and £3.97million).
The watch, unveiled in 2014, was designed to be Patek Philippe’s most intricate and complicated wristwatch in the company’s history and comprises 20 complications, including five chiming modes, a reversible case, two independent dials and six patented innovations.
Stallone’s Grandmaster Chime comes in its single sealed casing with a presentation box engraved with Stallone’s name as well as a certificate of origin confirming him as the original purchaser.
The lot also includes, among other things, product literature, a collection book, travel case, cufflinks, USB drive, and an Apple iPad with a leather case.
Elsewhere, Stallone’s Patek Philippe Nautilus 5711/1300A-001 is estimated to fetch between $200,000 and $400,000 (£159,000 and £318,000).
There is also an Audemars Piguet Royal Oak Tourbillon 50th Anniversary watch which could fetch between $100,000 to $200,000 (£79,500 to £159,000).
The Panerai Luminor Submersible, dubbed “Bronzo”, is estimated to sell for between $30,000 to $60,000 (£23,860 to £47,720) and is accompanied by a signed movie poster of The Expendables 2.
Stallone said: “I’ve had the privilege of owning some truly remarkable watches over the years, each with its own unique character and history.
“I enjoy the collecting process like so many others in this passionate community, who don’t just see watches as an accessory, but admire them for their history, craftsmanship, artistry – but most importantly – how they make them feel.
“Looking at these watches, I feel truly lucky to have owned them; they serve as a reminder that hard work pays off.
“While parting ways with this collection is bittersweet, I cherish that I’ve owned them with pride, and hope they will be appreciated and admired in their next homes.”
Geoff Hess, Sotheby’s head of watches, Americas said: “While many recognise Stallone as the legendary actor behind characters like Rocky Balboa and John Rambo, watch enthusiasts know the legendary actor to be a noteworthy, influential and truly passionate collector.
“Each watch in this collection is imbued with his appreciation for fine craftsmanship and artistry; from the intricate mastery of a Patek complication, to the unexpected elegance of a piece-unique Panerai.
“Not only does Sly’s collection offer discerning collectors the chance to acquire a rare work of horology, but one which has been handpicked and cherished by an American icon as well.
“It’s particularly thrilling to bring the astonishing Patek Grandmaster Chime, one of the most complicated wristwatches in the world, to the rostrum at Sotheby’s.
“With Sly being a personal friend, the opportunity to work with him and present this part of his collection to market is a privilege that eclipses virtually any watch project I’ve worked on in my career.”
Stallone’s collection is headlining Sotheby’s Important Watches auction, taking place in New York on June 5.
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