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Simon Leaf


Personal Profile

Simon is an experienced commercial Partner with a particular focus on the Technology and Sport sectors, where he leads the firm's offering, and is consistently recognised in these areas across the legal directories and beyond.

Simon specialises in advising clients (ranging from fast-growth start-ups to internationally listed companies, as well as governing bodies, Middle Eastern and African governments, major clubs, sponsors, intermediaries and athletes) on a range of transactional, IP and regulatory issues – including in particular, clients operating in the advertising, retail, property (including facilities management), healthcare and crypto industries.

He is widely seen as an expert in his field and consequently is often featured in the national and international press - including making appearances on Sky News, ITV and BBC, as well as being quoted across all of the major national news titles. Simon also recently co-authored the chapter on Financial Regulation in the leading Football Law textbook "Football and the Law" published by Bloomsbury Publishing.  

Simon is a mentor for the start ups taking part in MDR Lab and historically acted as semi-professional football referee; officiating on National Conference, Premier League Under 23 and Football League Reserve team matches.

Technology / Sports Technology

Simon has a breadth of experience advising on strategic transactions, often cross-border in nature. He has a long history of advising fast-growth SaaS/AI-led businesses on a range of commercial, IP and IT law matters. In particular, he has worked on several high profile proptech, adtech, retail, leisure, esports and betting & gaming deals.

Recent highlights include advising a fast-growth Swedish technology SaaS company on a number of its most important commercial agreements opposite its key customers and assisting several FTSE 100/S&P 500 companies on major IT outsourcing, global networks and data centre contracts.

Simon completed secondments with Dell and Tesco whilst at his previous firm.


Simon regularly works on significant broadcasting matters, image/digital rights agreements, sponsorship arrangements and international transfers.

Recent experience includes acting on what has been reported as boxing's first ever billion dollar deal, negotiating a major Premier League sponsorship contract for a fast growing African country, advising a high-profile player on reportedly one of the top three largest contracts in Premier League history  and assisting on multiple F1-related matters (including negotiating a naming rights deal for a major F1 team and a range of commercial/drivers contracts for a number of drivers).

On the regulatory side, he advises clients on an array of issues including Financial Fair Play, Third Party Ownership and Intermediaries Regulations, as well as several governing bodies and other non-sports clients on a wide selection of commercial law and privacy-related matters.


Key Experience

Recent Technology Experience
  • Drafted and negotiated of a number of major network service integrator and provider contracts for several FTSE 100 and S&P 500 clients on both the supplier and customer side
  • Supported a number of innovative PropTech, HealthTech and AdTech companies on a range of contractual law and privacy related matters – including advising on key reseller and distributor relationships
  • Provided a number of the Firm's betting and gaming clients with advice on IT/IP and data licensing arrangements
  • Assisted a fast growth Swedish SaaS provider with some of its most important commercial agreements (including the development of its AI business) – effectively acting as their UK GC for an extended period of time
  • Advised a global multi-channel retailer on a number of its most important commercial and technology contracts – including its media buying/creative agency agreements, check-out software/hardware/maintenance agreements and distribution contracts
  • Worked with a NASDAQ-listed technology supplier on an applications development agreement opposite a major international bank
  • Acted for a listed vehicle retail and logistics provider on an exclusive outsourcing and commercial agreement opposite a FTSE 100 international bank
  • Supported one of the world’s largest media, digital and creative communications agencies, a FTSE250 events company and a major internationally listed services and distribution company on a number of high profile commercial technology deals involving the purchase of data centre and cloud services opposite a number of different suppliers
Recent Sports Experience
  • Acted for a major African country in relation to its UK sports sponsorship activities
  • Advised the sports ministry of a prominent middle eastern country on the hosting of a number of major sporting events
  • Acted for one of the world's largest social media companies on a range of issues arising from its move into acquiring sports and related rights
  • Supported a number of Premier League and Championship clubs on compliance with financial regulations – including, in particular, FFP-related rules arising from COVID-19
  • Worked with several high-profile athletes and intermediaries across a range of sports on transfer, image rights, sponsorship and contractual-related issues – including advising a high-profile player on reportedly one of the top three largest ever contracts signed in Premier League history and a number of agents on the new FIFA Football Agent Regulations (FFAR)
  • Acted for the leading provider of utility tokens in the world of sport on a range of commercial, advertising and financial regulatory-related matters, as well as advising a number of other crypto/NFT-focussed clients on their most important legal matters (including as part of the Premier League's RFP for digital collectibles)
  • Advised on what is reported to be boxing's first ever billion dollar OTT broadcasting deal
  • Assisted a number of major betting and gaming clients on sponsorship/naming rights, data and commercial law issues – including across multiple sports
  • Provided legal assistance to several governing bodies on a range of legal issues – including some of the client's most important contracts with athletes, undertaking regulatory reviews and providing GDPR-related advice
  • Advised another governing body on resolving a multi million pound multi-party dispute and an external investment into the sport by a well-known private equity group
  • Worked for a number of fast-growth sports technology and esports clients on a range of legal matters
  • Advised a large blue chip client on a major Premier League shirt sponsorship deal and have advised a number of clubs on their template commercial partner agreements

Career History

Partner, Miscon de Reya LLP
Legal Director, Mishcon de Reya LLP
Associate, Berwin Leighton Paisner LLP
Trainee, Berwin Leighton Paisner LLP
University of Cambridge, Management Studies

Articles and Publications

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