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SINGAPORE — “Welcome. Please sit in the Spitfire chair.”

Dr. Bernard Cheong, a physician and probably one of the world’s quirkiest watch collectors, gestured at a red leather seat from the cockpit of a former Royal Air Force plane. It sat on a covered porch at his home, along with a mounted water buffalo head, antique ice-making machines, some hoverboards and a handful of watches — just a small part of the collection he estimates to be worth $15 million to $20 million, most of which he keeps at a secure site.

Just home from work at his medical clinic, Dr. Cheong poured the first of several Chivas on ice and settled at a stainless-steel seat-and-table structure, the vibration-free platform he usually uses to inspect his watches. He had the 3-ton piece designed by a Canadian-Chinese sculptor and, once it was fabricated, air-lifted onto his porch — “We had to remove the roof,” he explained.

Dr. Cheong, 58, is one of the few self-taught watch enthusiasts accepted by Switzerland’s elite industry organizations. In 2002, he helped create a more transparent jury system for the Grand Prix d’Horlogerie de Genève, the annual watchmaking competition. In 2011, he became the first lay expert — and the first Asian — to be appointed as an ambassador for the Fondation de la Haute Horlogerie in Geneva.

He is an oddity in the rarified world of top watch collecting: He is not European, he is not an industry professional and he does not have inherited wealth. As the co-owner of a chain of medical clinics, he would most likely describe himself as comfortably affluent, but certainly not in the ranks of the global elite. When he started attending watch fairs in the late ’90s, he paid for his own economy-class tickets to Switzerland.

He is as passionate about watches online as he is in person and began posting on the Singapore-based watch website TimeZone in the mid-’90s. His own blog and Facebook page have dazzling photos of his acquisitions, as well as insider tips that the industry may or may not appreciate. (One watch-enthusiasts’ online forum has essentially barred him for what it described as being too self-promotional.)

He and his wife Dolly Ong are regulars on the Singapore society scene, often photographed with something very pricey strapped to their wrists.

“Why am I famous?” he asked rhetorically. “Not because I’m some rich famous dude but because I’m a loudmouth. When I say something bad — like ‘This watch isn’t worth a fraction of its sales price’ — I’m lambasted.”

Dr. Cheong says that like all good collectors, he looks for quality, rarity, beauty and price — and also is motivated by the thrill of the hunt.

Among his most prized acquisitions are two No. 00/11 watches; the zero is used to label the watchmaker’s own piece in an 11-item limited edition.

One is a Greubel Forsey Invention Piece 1, a platinum watch with a double tourbillon, that Dr. Cheong said cost him $2.2 million in 2014. (He said he saved for nearly a decade and sold some less-valuable pieces from his collection to afford it.) “This actual piece was on Robert Greubel’s wrist,” he said of the Swiss watchmaker. “I will not sell it for profit. It should end up in a museum.”

His other “00/11” belonged to Vianney Halter, the French-born watchmaker who has a strong cult following. “There should be more people like Bernard Cheong in the world,” Mr. Halter wrote in an email interview, praising the doctor for supporting independent watchmaking.

Dr. Cheong’s collection also includes classics from Rolex, Cartier and Omega, as well as historic pieces like a 19th-century Hamilton, a pocket watch made in the United States, and another pocket watch made of cheap metal in Germany during World War II.

Many of the doctor’s watches are unusual contemporary designs, especially those with a steampunk look. One is a Devon Tread One, an American-made watch whose face is a blocky black square with stark white numbers. Another is a red-gold Cabestan, which is run with old-fashioned winch-and-chain mechanisms, made in Switzerland. And he has a timepiece by the independent Swiss watchmaker Romain Jerome that includes metal from the Titanic.

Dr. Cheong’s first watch, a Flyback Seiko Chronograph, was a gift from his parents, a sculptor and a nurse, when he was 15. At 23, he got his first paycheck as a doctor and used part of it to make his first watch purchase, an Omega Seamaster Titanium. He still has both watches, their bands now faded and too tight, their cases strangely small against the giant models of today.

He began collecting in the 1980s and has many stories of those early days. “The time I started collecting, it was just luck,” he said, describing, for example, how he bought a lot of Panerai watches in the ’80s and early ‘90s from a Singapore shop that was having trouble moving stock.

“I had a gut feeling,” he said. “I just let them sit in my warehouse until 1998. One day I thought, ‘Goodness! I forgot about those watches!’ So I released them via auction a bit at a time.” He says he bought the Panerais for about $3,000 each, and the best ones ended up selling for almost $90,000 each.

In an age of smartphones and Apple Watches, the mechanical timepieces Dr. Cheong collects are, practically speaking, no longer necessary. He does not feel, however, that the march of technology will diminish the connoisseur’s love of luxury watches.

“When photography was invented, some people said, ‘What’s the point of painting? A photograph will always be easier and more accurate,”’ he said. “But photography didn’t kill art. There are still great painters, and their works have only gone up in price.”

On his own wrist the day of the interview was a Seiko, the same brand he coveted as a 15-year-old. Only this time, his Seiko had parts carved from a single piece of synthetic diamond. “Don’t tell anyone,” he said, sotto voce. “This model is not out yet.”