Weird and wonderful debentures – Wimbledon and beyond

The first – and so far only – time I featured debentures, I wrote about the famous securities issued by Wimbledon.

At the time, pandemic lockdowns had pushed them out of favour. Prices were down, and supply was plentiful.

Since then, Wimbledon Debentures have staged a remarkable recovery. Their value has tripled since 2024.

What exactly are Wimbledon Debentures? Is it too late to invest in them? And what other opportunities might be hiding in the obscure world of debentures?

"Deben-what?"

Today, debentures are no longer a familiar category of security.

Their name, however, gives away their origins. It is derived from the Latin debentur ("they are owed"), a term originally used to describe formal acknowledgements of indebtedness. Initially, it referred to money owed by the government or the Crown to soldiers and others entitled to payments for services rendered. From the 18^th century onwards, the term came to be associated primarily with debt issued by companies.

The obvious question is: what is the difference between a debenture and a bond?

There is no sharp distinction, and the terminology differs somewhat between the UK and the US. Broadly speaking, debentures are unsecured and rely on the issuer's creditworthiness rather than specific collateral. They are often issued to finance a particular project or expansion and therefore generally carry more risk than secured bonds.

Today, debentures receive little attention.

That was different in the 19^th and early 20^th centuries.

In 1894, Edward Manson published his seminal work "Debenture Stock of Trading and Other Companies". In the preface, he observed: "Debentures have now become an incident of daily life to lawyers and businessmen."

Another excellent guide was Herbert W. Jordan's "Debentures – The purposes they serve and how they are issued". The copy in my library, published in 1924, is already the book's 11^th edition.

Two very rare originals from my own library.

In one particularly entertaining chapter, Jordan explored what he called "curiosity debentures":

• Golf clubs issued debentures secured against little more than their golf balls. He described this as the equivalent of saying: "I owe you much, I have nothing."
• Football clubs raised money against future ticket income – or "gate money", as it was known then. Jordan remarked: "Notwithstanding the somewhat precarious nature of the security, large sums have been raised in this manner."
• Churches issued debentures that were, in effect, advances against future collections. Jordan noted that charismatic preachers with greater "drawing capacity" often found it easier to raise money this way. He also pointed out that the idea was far from modern: a cuneiform deed dating from 344 BC, preserved in the British Museum, records a Babylonian temple raising money secured against future "temple revenue".
• Companies occasionally joined forces to issue a single debenture. Jordan observed that such arrangements were "liable to lead to complications" and added that "only few cases have occurred without either the Companies or the Debenture Holders being eventually in misfortune."

By now, readers will have realised just how "elastic" the term debenture has always been.

Jordan also warned that debentures created "many opportunities for defrauding others".

One particular type of debenture, however, has long stood apart.

In fact, it has been issued continuously since 1920.

Now in its 106^th year, it has brought both enjoyment and handsome financial returns to its holders – most of the time, at least.

Wimbledon – the King of Debenture issuers

Of all the debentures in the world, none is more famous than those issued by The All England Lawn Tennis Club PLC.

The company owns the tennis courts, grounds and buildings at Wimbledon. Formerly run as a charitable club, it is now a for-profit company. The world-famous tournament has been held there since 1877. Anyone who has visited the grounds will know what an extensive, modern and maintenance-intensive operation it is.

Whenever the club undertakes major investments, it raises money by issuing debentures. These are, in effect, unsecured, securitised loans that come with valuable privileges.

Debenture holders pay a substantial upfront amount, but receive no interest. Instead, they are granted a range of benefits:

• A fixed allocation of tickets for tournaments on specific tennis courts.
• Access to exclusive facilities, including VIP restaurants and reserved parking.
• A right of first refusal to subscribe to the next debenture issue, allowing holders to maintain their position once their current debentures expire.

Back in 2020, I published a detailed article titled "Oversupply of Wimbledon Debentures – your opportunity to invest?"

At the time, Wimbledon Debentures were unusually plentiful and comparatively cheap. The pandemic had forced the cancellation of that year's Championships. Fortunately for the club, it had taken out pandemic cancellation insurance following the SARS outbreak in the early 2000s. That foresight resulted in a GBP 100m insurance payout at a time when many sporting organisations were fighting for survival. Even so, investors feared that the market for live sporting events might be permanently damaged.

As I wrote at the time: "The time to try and strike a deal to 'join the club' (almost literally) would be now. The issue price of the Centre Court 2021-2025 issue was GBP 80,000. Right now, anyone looking to sell immediately would not be able to recover the issue price. Due to corona, the market is quite out of whack!"

The latest issue, originally sold for GBP 80,000, could be bought for only GBP 74,000. That was highly unusual, as Wimbledon Debentures had historically traded at roughly twice their issue price. In effect, buyers could have entered the market at half the normal price.

Naturally, my assessment came with several caveats. The market has limited liquidity, and these securities would primarily appeal to tennis buffs. Nevertheless, the investment case was genuine:

• Debenture holders can sell their tournament tickets, typically generating an attractive return on their invested capital. Specialist agencies can handle these sales, so there is no need to list tickets yourself.
• Few holders can personally make use of every ticket included with the debenture. Selling at least some of them is therefore a normal part of ownership.
• The purchase price is high enough that even wealthy investors are unlikely to ignore the financial aspects altogether.
• Since Wimbledon Debentures almost always trade above their issue price, the embedded right to subscribe to the next issue at par has significant value. Some families have maintained continuous ownership across several generations.

Taken together, these characteristics made Wimbledon Debentures an unusually attractive opportunity when they briefly fell out of favour.

Those who entered the market during that period will have done exceptionally well.

Looking back, fears that the pandemic would permanently damage live sporting events proved far too pessimistic (remember Dr. Fauci suggesting we "should never shake hands again"?). Demand has returned with remarkable strength. In fact, sporting events have arguably become even more popular – and more expensive – than before.

During 2024 and 2025 in particular, Wimbledon Debentures staged a spectacular recovery:

• The memory of lockdowns faded into the rear-view mirror.
• The growing rivalry between ATP No. 1 Jannik Sinner and ATP No. 2 Carlos Alcaraz generated enormous public interest.
• Premium sporting events increasingly came to be viewed as a form of luxury entertainment.

The value of debentures naturally declines as they approach their expiry date, and different issues come with slightly different privileges. This makes historical price comparisons somewhat difficult. Even so, Bloomberg captured the broader trend when it reported on 23 June 2026: "Wimbledon debenture prices have more than tripled in two years, with the current price at GBP 380,000".

Past debenture issues came with a fascinating guidebook.

Just how special these securities are became apparent in late 2025, when the British government created a carve-out in new legislation. As part of its efforts to curb ticket scalping, the Labour government banned the resale of sporting tickets above face value. Wimbledon Debentures, however, received a specific exemption.

To survive even this onslaught illustrates the remarkable resilience of this unusual investment.

After more than a century of continuous issuance, Wimbledon Debentures appear likely to remain a quirky, lucrative investment for some time to come.

Readers interested in learning more can consult the resources listed in my original 2020 article. Since little moves quickly in the tradition-rich world of Wimbledon, they remain just as relevant today. Or see this overview of the current Wimbledon Debenture market, provided to me on 15 July 2026 by Dowgate Capital, the London brokerage firm that handles these trades.

Scoping out lucrative niches

Debentures are, of course, a niche subject.

I'll also be the first to point out the obvious drawbacks of Wimbledon Debentures. They are illiquid, complex, and difficult to scale.

Nonetheless, my readership has always had a particular appreciation for these kinds of outlier investments.

For example, I continue to receive enthusiastic feedback about my 2022 article on "cemetery land share certificates". These are OTC-traded securities in the US – a remnant of a long-bygone era. Think late-19^th-century IPOs of cemeteries, which at the time were regarded as a lucrative investment. Even though I do not know of a single reader who has actually managed to acquire one of these land share certificates – largely because of the high barriers to entry in this part of the OTC market, rather than a lack of certificates available for trading – I continue to receive comments saying that this is one of the most fascinating articles I have ever published.

Surely there must be other oddball debentures and similarly quirky securities out there?

In fact, one such investment was presented at the Weird Shit Investing conference in London last month. Tim Bergin of Calderwood Capital introduced his firm's investment in California Carbon Allowances, a niche asset class that is considerably more liquid and scalable than Wimbledon Debentures. You can find a summary of the investment case in the Weird Shit Investing Manual 2026.

Tim will also be speaking at the upcoming Weird Shit Investing Online conference on 28 July 2026. Like all the other speakers, he will present a new investment idea rather than simply repeating his presentation from June. Make sure to book your place!

Discover the next overlooked niche

If you enjoyed today's excursion into the curious world of debentures, you'll feel right at home at Weird Shit Investing Online.

With 21 speakers, this is the biggest Weird Shit Investing programme to date.

Don't miss:

• Andrew Walker, author of the highly respected Yet Another Value Blog and one of the best-known voices in event-driven value investing.
• Jonathan Tanne, CIO of Tangible Investment Management, specialising in deeply undervalued, asset-backed businesses.
• Michael Fritzell, founder of Asian Century Stocks and one of the leading independent commentators on Asian equities.
• Sara, founder of TripleS Special Situations Investing, specialising in bankruptcies, litigation and other quirky investment situations.
• Swen Lorenz (yours truly), presenting two original investment ideas from well outside the mainstream.

And many more!

Join us live, ask questions during the Q&A sessions, or watch the recordings afterwards at your convenience.

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