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Our SiGMA series, “The Online Gambling Industry: Tales from the Past,” continues with more insights from Ian Sherrington. In this article he examines why the brick-and-mortar bookmakers were so slow on the uptake when it came to online sports betting.
The late 1990s marked the beginning of online sports betting, with the launch of the first online sportsbook in 1996.
Pioneers like Intertops soon proved that a profit could be made in this new market, but established bookmakers such as Ladbrokes and William Hill were somewhat slower to follow, their first serious UK-based websites were eventually launched in 2000.
Their delay in entering the digital space was shaped by a complex mix of regulatory, technological, reputational, and strategic concerns.
One of the key deterrents was regulatory uncertainty. Governments had yet to define clear rules for online gambling, and traditional bookmakers, closely tied to their brick-and-mortar licenses, feared jeopardising their compliance standing. Without a solid legal foundation, venturing online posed a significant risk.
Technological limitations also played a role. While startups were built from the ground up for the internet, established betting firms were encumbered by legacy systems and infrastructure. Building a secure, scalable online sportsbook from scratch required major investment and new expertise, resources they were reluctant to commit without assurance of long-term viability.
There was also a strategic fear of cannibalising their core business. Traditional bookmakers generated most of their revenue through physical betting shops, and there was a genuine concern that online betting would undercut this channel rather than complement it. Their conservative approach was further reinforced by concerns over brand reputation. Early online gambling was often associated with unregulated or offshore operations, and established firms hesitated to risk their hard-earned public trust by jumping into what many perceived as a murky or even illicit space.
Nevertheless, some took bolder paths. William Hill briefly operated from Antigua, leveraging one of the first online gambling licenses under the Free Trade & Processing Act of 1994. But due to regulatory pressure, they soon withdrew.
Meanwhile, Victor Chandler, a pivotal figure in online betting’s offshore expansion, moved his business to Gibraltar, where the low-tax regime allowed him to offer UK customers tax-free betting.
This gave his business a significant edge over domestic competitors burdened by the UK’s 9 percent betting tax. Chandler’s bold move led to major policy change: in 2001, the UK abolished the tax on punters and shifted to taxing bookmaker profits instead.
The early 2000s marked a turning point. Regulatory frameworks such as the UK Gambling Act of 2005 began to legitimise and stabilise the industry, while technological advancements made online operations more secure and efficient.
With risk reduced and digital infrastructure maturing, traditional bookmakers finally moved online.
Ultimately, while their cautious entry may have cost them a head start, companies like Ladbrokes and William Hill used their strong brands and deep pockets to catch up quickly.
Today, they are key players in a global online betting market, proof that strategic patience, paired with adaptability, can pay off.
PART ONE: The online gambling industry’s tales from the past
PART TWO: The first online wager
PART THREE: Exploring the origins of online gambling jurisdictions
PART FOUR: How the law reacted to the rise of online gambling
PART FIVE: How online gambling used emerging web technologies
PART SIX: The shared high of love and gambling