• "Simon is not only technically adept and someone who quickly grasps complicated issues, but he's always somebody who demonstrates an awareness of the bigger commercial picture." (Chambers UK, 2025)
• "Simon Oakes knows the law very well and is indefatigable in the face of adversity." (Chambers UK, 2025)
• "He's super knowledgeable about the law and the products and the issues in financial service claims." (Chambers UK, 2025)
• "He is an immense talent. He really knows his stuff and is the perfect senior junior to deploy on a tough fraud case. He is also a gifted advocate and judges really listen when he speaks." (Legal 500, 2025)
• "Simon is not only technically adept and quickly grasps complicated issues, but always demonstrates an awareness of the bigger commercial picture – be that what tactics to employ to create an opportunity for a commercial settlement or to protect the client’s wider commercial interest rather than simply focus on the case at hand."  (Legal 500, 2025)
• "Confident, good with clients, works hard to find solutions, not afraid of a difficult case, and seeks to be creative with arguments - clear advice and drafting." (Legal 500, 2024)
• “An exceptionally intelligent individual who adopts a personable approach and can explain complex legal points clearly and simply to lay clients.” (Chambers UK, 2024)
• "He is super present and great to work with, a real team player. Clients find him very impressive." (Chambers UK, 2023)
• "Simon is extremely hard working, an excellent support to his leader but also able to stand on his own two feet and argue very succinctly in court. He is always well-liked by clients, and is very user-friendly." (Legal 500, 2023)
• "Simon is unflappable; he is realistic; confident and self-assured beyond his years. He was a real asset to the team and much admired by the client." (Legal 500, 2023)
• “He is very reliable, very sensible and a future star. The quality of his work is impressive.” (Chambers UK, 2022)
• "Simon has a very good brain and thinks outside of the box - one to watch." (Legal 500, 2022)
• "Simon has excellent technical expertise, is always up to date on case law in the area and is willing to think outside the box to push the boundaries of a case as far as legitimately possible." (Legal 500, 2022)
• “He’s one to watch. Highly intelligent and always responsive.” (Chambers UK, 2021)
• “Simon is all about the detail and he grapples with complex legal issues with ease. He is tenacious when dealing with an opponent, yet commercial when dealing with clients and their intended objectives.” (Chambers UK, 2021)
• "An effective and valuable junior counsel, who is a very competent young barrister with the ability to think quickly." (Legal 500, 2021)
• "Miles above his call level when it comes to his experience and offering, both from a client perspective and from that as instructing solicitor." (Legal 500, 2021)

Simon is instructed across the full range of commercial dispute resolution, with a particular emphasis on complex civil fraud cases:

• Obtaining Worldwide Freezing Injunctions 
• Lowry Trading v Haycox (2024, High Court) Representing a property developer accused of operating a fraudulent Ponzi scheme: allegations of deceit, conspiracy, breach of trust 
• A v B (2024, LCIA Arbitration) Acting for a multinational company in a €250 million international arbitration relating to an M&A transaction, involving allegations of market manipulation, anticompetitive behaviour, misrepresentation and apparent bias. 
• Providing an opinion to parties under a contractual dispute resolution mechanism as to liability and quantum in a breach of warranty SPA claim, arising out of alleged ‘call-clipping’/overcharging in the care sector.
• Contractual dispute relating to aircraft tyres which exploded upon take-off, causing around £16 million of damage to the aircraft.
• Acting in multiple, multimillion pound High Court engineering disputes relating to the condition, maintenance, and corrosion of thin-walled carbon steel (TWCS) pipework in commercial premises, including Burges Salmon v Glass Wharf (2023, High Court), with Julian Greenhill KC. 
• Advising in respect of the correct construction of various insurance policies. 
• Breach of warranty claims arising out of share purchase agreements.
• Appearing in the High Court in a director/shareholder derivative claim involving issues of injunctive relief and alleged breach of directors’ duties. 
• A v B (2022): Successfully obtaining an injunction to restrain presentation of a winding-up petition, in connection with a very high-value disputed debt which is subject to arbitration. The case involved allegations of market distortion; Salford Estates (No.2) Ltd v Altomart Ltd [2014] EWCA Civ 1575 applied. With Paul Downes QC. 
• Circumference Investments (Europe) Ltd and others v Martin [2021] EWHC 2691 (Ch), a successful application to give effect to the legal and living expense exceptions in an English worldwide freezing order in preference to a competing Luxembourg freezing order, distinguishing Tidewater Marine v Phoenixtide Offshore [2015] EWHC 2748 (Comm).
• Lombard North Central v Airbus [2021] EWHC 2025 (Comm): a multi-million pound commercial dispute involving issues of alleged product liability, contractual construction and a novel issue of French limitation law. With Matthew Reeve. 
• Advising in multiple, high-value business cases as to whether negotiations had led to completed contracts, together with issues of estoppel, misrepresentation and unjust enrichment. 
• Acting in an ongoing claim involving allegations of push payment fraud.
• A v B [2019] 10 WLUK 65: successfully resisting CPR 31.16 application for pre-action disclosure in high-value dispute about a failed hotel sale.
• Acting for Water Plus and United Utilities in cases relating to water supply, drainage, sewerage charges and the reorganisation of the water industry
• Acting and appearing as sole advocate in several cases involving issues of corporate insolvency, preferential payments, equitable charges, and enforcement of personal guarantees.
• Advising as to conflict of laws and breach of warranty of authority in a complex wet shipping dispute.
• Advising upon contractual interpretation and scope of duty in a commercial construction dispute.
• Advising and appearing as advocate in a number of Chancery Division shareholder disputes, involving allegations of deceit, unfair prejudice and forfeiture of shares.
• Munroe K Limited & Anor v Bank of Scotland: multi-million pound Commercial Court case, involving allegations of fraudulent misrepresentation. With Alan Gourgey QC (Wilberforce Chambers).
• Aldersgate & Ors v Bank of Scotland & Anor [2018] EWHC 2601 (Comm): a Commercial Court claim in excess of £100 million, alleging allegations of deceit and negligent misrepresentation arising out of benchmark manipulation. The case also raised ancillary issues as to the status of findings by global regulators, and attempts to withdraw pleaded admissions. With Stephen Auld QC (One Essex Court).
• Appearing for major hotel company in a series of timeshare cases involving contractual issues, the law of unincorporated associations, fundamental change to the purpose of a club, unfair terms, misrepresentation and conflict of laws.
• A pre-employment misrepresentation claim, brought against a fund manager in the High Court.
• Representing the directors of an off-shore Investment Manager and off-shore Fund in a significant high-value shareholder dispute.
• Hermes Ors v Banco Espirito Santo. Acting for investors in a civil fraud claim against the failed Portuguese bank and its former directors.
• Advising on matters arising out of a film investment scheme.

Simon has been instructed in many of the most significant banking cases of recent years. He has a particular expertise in, and often gives seminars on, cases involving Authorised Push Payment (‘APP’) fraud. 
Simon’s recent work includes:

• Acting against a bank in a case involving allegations of state embezzlement and breach of bank mandate.
• Acting for and against major banks in cases involving allegations of authorised push payment fraud, and agent/principal fraud (following Quincecare and Philipp v Barclays).
• ECU v Goldman Sachs & Others (2021, High Court). ‘Forex Rigging’ claims arising out of allegations of manipulation of the Foreign Exchange market (in particular, the ‘spot’ FX Rate), and sharing of confidential information. 
• Boyse (International) Ltd v Natwest Markets Plc [2020] EWHC 1264 (Ch), where the Court considered limitation principles (and in particular, reasonable diligence) in the context of allegations of commercial fraud. Permission to appeal has been granted.
• Acting for and against spread-betting platforms in cases alleging breach of regulatory duty.
• Acting in Upper Tribunal proceedings in respect of the validation and enforceability of timeshare loans (pursuant to s.28A FSMA 2000) entered into in breach of the FCA’s ‘general prohibition’.
• Advising in respect of damage caused to a highly-successful business by a bank’s appointment of administrators and receivers.
• Opining in a number of very high value High Court cases - for the benefit of the Court - as to the impact of Brexit on the reasonable security of periodical payments made by insurers based in Gibraltar or the EEA, with a particular emphasis on likely cover by the Financial Services Compensation Scheme (FSCS)
• Advising and conducting advocacy in an ongoing high-value Commercial Court dispute arising out of benchmark interest rate manipulation
• Scarborough Group Developments Ltd v Bank of Scotland & Anor: a very high value commercial dispute involving allegations of benchmark interest rate manipulation
• Munroe K Limited & Anor v Bank of Scotland: multi-million pound commercial fraud case, involving issues of fraudulent misrepresentation. With Alan Gourgey QC (Wilberforce Chambers)
• City & Country Residential Limited v Lloyds Bank: multi-million pound deceit and misselling case, in particular involving allegations of LIBOR manipulation. 
• Aldersgate & Ors v Bank of Scotland & Anor [2018] EWHC 2601 (Comm): a Commercial Court claim in excess of £100 million, alleging allegations of fraudulent and negligent misrepresentation arising out of benchmark manipulation. The case also raised ancillary issues as to the status of findings by global regulators, and attempts to withdraw pleaded admissions. With Stephen Auld QC (One Essex Court).
• Macdonald Hotels Limited v Bank of Scotland: a very high-value, Financial List banking dispute involving allegations of breach of a shareholders’ agreement. With Richard Lissack QC (Fountain Court). See https://www.law360.com.
• Hockin v Royal Bank of Scotland: a £55m Financial List banking case concerning interest rate products and the bank’s Global Recovery Group (‘GRG’), and involving issues of misrepresentation, LIBOR manipulation, unlawful means conspiracy and implied duties of good faith. With David Reade QC (Littleton Chambers).
• The LIBOR test case of Graiseley Properties Ltd v Barclays Bank Plc, Deutsche Bank AG v Unitech Global Ltd [2013] EWCA Civ 1372 (CA), in the Court of Appeal and in the High Court (with Stephen Auld QC). One of The Lawyer’s ‘Top 20 cases’ of 2013.
• Desiman Ltd v BOS, HBOS and Lloyds Bank: a significant banking matter involving issues of mis-selling, LIBOR misrepresentation, appointment of administrative receivers and bad faith. The case also involved an examination of the Bank’s Business Support Unit. With Stephen Auld QC.
• Ford, Owen & Johnson v Financial Conduct Authority [2016] UKUT 0041 (TCC): acting for the former compliance officer of Keydata (Johnson) in a reference to the Upper Tribunal.
• Atwal v Bank of Scotland: an High Court interest rate hedging dispute, involving allegations of misselling.
• FOREX investigation: acting for individuals under investigation by global regulators in relation to Forex matters.
• Advising and drafting pleadings across a range of high-value interest rate swap claims, including on matters arising out of the FCA Review into the mis-selling of Interest Rate Hedging Products (‘IRHPs’).
• Acting for a major international law firm conducting a s.166 FSMA Skilled Person’s review into the mis-selling of IRHPs and consequential losses.

In 2012 Simon was seconded to the General Counsel’s Division of the Financial Services Authority for 9 months, drafting Handbook rules and guidance in relation to Collective Investment Schemes. Simon’s role included liaising with FSA policy-makers, advising on partnership law, and negotiating the drafting of legislation with HM Treasury and Parliamentary Counsel.

• A v B (2024, LCIA) Acting for a multinational company in a €250 million international arbitration relating to an M&A transaction, involving allegations of market manipulation.  
• Advising in a dispute about alleged deceit and breach of trust, relating to the theft of shares in land on a tropical island.
• Obtaining Worldwide Freezing Injunctions
• Lowry Trading v Haycox (2024, High Court) Representing a property developer accused of operating a fraudulent Ponzi scheme: allegations of deceit, conspiracy, breach of trust 
• Acting against a bank in a case involving allegations of state embezzlement and breach of bank mandate.
• Acting for and against major banks in cases involving allegations of authorised push payment fraud.
• Advising in respect of claims against banks arising out of frauds on the principal/customer (following Quincecare and Philipp v Barclays).
• Advising and appearing as advocate several Chancery Division shareholder disputes, involving allegations of deceit, unfair prejudice and forfeiture of shares. 
• Munroe K Limited & Anor v Bank of Scotland: multi-million pound Commercial Court case, involving allegations of fraudulent misrepresentation. With Alan Gourgey QC (Wilberforce Chambers).
• Aldersgate & Ors v Bank of Scotland & Anor [2018] EWHC 2601 (Comm): a Commercial Court claim in excess of £100 million, alleging allegations of deceit and negligent misrepresentation arising out of benchmark manipulation. The case also raised ancillary issues as to the status of findings by global regulators, and attempts to withdraw pleaded admissions. With Stephen Auld QC (One Essex Court).
• Hermes Ors v Banco Espirito Santo. Acting for investors in a civil fraud claim against the failed Portuguese bank and its former directors.

• 2025, High Court contractual dispute relating to aircraft tyres which exploded upon take-off, causing around £16 million of damage to the aircraft.
• Lombard North Central v Airbus [2021] EWHC 2025 (Comm): a multi-million pound commercial dispute involving issues of alleged product liability, contractual construction and a novel issue of French limitation law. With Matthew Reeve.
• Significant expertise in catastrophic multi-million pound personal injury cases, including advising and drafting complex Schedules of Loss.
• Acting for airlines in passenger claims brought under Regulation (EC) No 261/2004. 
• Claims involving accidents and illnesses suffered while on holiday abroad.  
  

Simon’s current and recent work includes:

• Various shareholder and joint venture disputes, including issues of unfair prejudice, breach of fiduciary duty, deceit and injunctive relief.
• Obtaining injunctive relief in the High Court, including restraining the presentation of winding up petitions.
• Viavi v Shannan & Others [2018] EWCA Civ 681: Successfully resisting an appeal, as to the validity of the substitution a principal employer and consequent questions as to whether subsequent deeds were validly executed by the correct employer company. Also involved questions relating to the Re Duomatic principle, and estoppel by deed (led by Nicolas Stallworthy QC).
• Viavi v Shannan & Others [2016] EWHC 1530 (Ch) (led by Nicolas Stallworthy QC).
• Directors’ disqualification hearings in the High Court.
• Successfully applying for annulment of bankruptcy petitions.

• Acting in a High Court claim by property developers arising out of negligent solicitor advice by solicitors in relation to a landlocked building development.
• A professional negligence claim, arising out of an alleged failure to advise in relation to pension scheme amendments.
• A professional negligence claim, arising out of a failure to validly amend a scheme deed (with Nicolas Stallworthy QC).
• A professional negligence claim against the administrator of a personal pension scheme.

• Advising about the Third Parties (Rights Against Insurers) Act 2010, and fair presentation of risk under the 2015 Insurance Act.
• Advising in various cases as to the correct interpretation of insurance policies
• Advising as to allegedly reckless misrepresentation of risk to insurers by an SME
• Opining in a number of very high value High Court cases - for the benefit of the Court - as to the impact of Brexit on the reasonable security of periodical payments made by insurers based in Gibraltar or the EEA, with a particular emphasis on likely cover by the Financial Services Compensation Scheme (FSCS)

Simon was seconded to the Pensions Regulator in 2015, working across the Regulator’s legal teams. He built up a good knowledge of the Regulator’s approach, in particular whilst working on pensions liberation / scams, avoidance and scheme funding matters, as well as advising in relation to statutory interpretation and the exercise of the Regulator’s powers.

• Devon and Somerset Fire & Rescue Authority v Howell & Anor [2023] EWHC 257 (Ch): Successfully defending HMRC’s interpretation of the meaning of "actual or prospective right" to pension benefits under the Finance Act 2004, in the context of unauthorised payment charges
• Advising as to the correct interpretation of a statutory pension schemes, and as to pension age entitlement in the context of unauthorised payment charges.
• Viavi v Shannan & Others [2018] EWCA Civ 681: Successfully resisting an appeal, as to the validity of the substitution a principal employer and consequent questions as to whether subsequent deeds were validly executed by the correct employer company. Also involved questions relating to the Re Duomatic principle, and estoppel by deed (led by Nicolas Stallworthy QC)
• Viavi v Shannan & Others [2016] EWHC 1530 (Ch) (led by Nicolas Stallworthy QC).
• Acting for the Pensions Regulator on matters including prohibition of Scheme Trustees, and Auto-Enrolment penalties.
• Advising on the enforceability of non-pensionability agreements, and on proposed amalgamation of trustee boards of several different schemes.
• A professional negligence claim against the administrator of a personal pension scheme.
• Advising members of various schemes on potential complaints to the Pensions Ombudsman

Providing employment law advice to well-known companies and conducting advocacy in the Employment Tribunal.