More about me

  • Counsel for physicians and surgeons in defence of claims that they were negligent in the performance of their professional practices, including 2005 MBQB 157, 2006 MBQB 194, 2006 MBCA 30, 2019 MBQB 19
  • Counsel for realtors and real estate agents in defence of claims that they were negligent in the performance of their professional practices, including 2015 MBQB 136, 2020 MBQB 23, 2021 MBCA 51, 2021 MBQB 24
  • Counsel for defendants in responding to a claim of an economic loss of chance in respect of development property 2020 MBQB 23 and 2021 MBCA 51
  • Counsel for defendants in respect of valuation of development property 2021 MBQB 24
  • Counsel for physicians in litigation to interpret and apply certain terms and provisions of The Mental Health Act (Manitoba) 2006 MBCA 28
  • Counsel for physicians in litigation to interpret and apply certain terms and provisions of The Limitation of Actions Act (Manitoba) 2014 MBCA 19
  • Counsel for the plaintiff in litigation to interpret and apply contractual provisions in the context of an independent contractor relationship, which resulted in a decision from the Manitoba Court of Appeal that is one of the leading cases on the principles of contractual interpretation 2011 MBCA 80
  • Counsel for international agricultural supply corporation in product supply/product liability disputes
  • Counsel for corporations in a variety of different litigation proceedings, including commercial disputes and addressing shareholder matters and complaints, including corporate oppression claims/shareholder disputes
  • Counsel for appraisers in response to various claims relating to property valuation and appraisal services
  • Counsel for multiple different corporations, financial institutions and insurers all of whom have taken injunction proceedings to secure orders freezing and seizing assets for recovery in the case of fraud or dishonest conduct or email hacking scams
  • Counsel for financial institutions in actions taken to recover from events of employee dishonesty
  • Counsel for several financial institutions, including banks and credit unions as well as for other public and private lenders, to assist in recovery efforts and collection proceedings
  • Counsel in a variety of commercial litigation disputes, including contractual disputes, lease disputes, agreements for purchase and sale and other commercial transactions
  • Counsel for commercial landlords in landlord tenant disputes, including issues relating to default, rental arrears, termination of leases
  • Counsel for commercial landlord in successfully defending an injunction request by an overholding tenant
  • Counsel for various owners and contractors in the course of construction disputes, lien actions and contractual interpretation litigation
  • Counsel on arbitrations in both commercial disputes and construction matters
  • Counsel for homebuilders successfully resisting motions for injunctions to halt development
  • Counsel for real estate developers in relation to disputes relating to development issues with adjoining property owners, municipalities and/or provincial planning districts

Gregory has significant experience in many areas of civil litigation, including work for a variety of different types of professionals both in terms of defending malpractice/negligence lawsuits and responding to proceedings involving their governance and licensing. He also has significant experience in general commercial litigation, including corporate matters, shareholder disputes, banking litigation, property matters and collection proceedings.

Gregory has appeared before all levels of Court in the Province of Manitoba, as well as the Federal Court of Canada and the Tax Court of Canada. He also regularly appears before various different administrative tribunals and quasi-judicial boards.

  • Member, The Law Society of Manitoba (Manitoba)
  • Member, Manitoba Bar Association (Manitoba)
  • Member, Canadian Bar Association

  • Recognized in the 2025 edition of the Best Lawyers in Canada (Director and Officer Liability Practice, Insurance Law)
  • Recognized in the 2025 edition (and since 2024) of the Best Lawyers in Canada (Corporate and Commercial Litigation)
  • Recognized in the 2025 edition (and since 2019) of the Best Lawyers in Canada (Personal Injury Litigation Law)
  • Recognized in the 2025 edition (and since 2021) of Chambers Canada (General Commercial Litigation – Manitoba)
  • Recognized in the 2025 edition (and since 2019) of the Canadian Legal Lexpert Directory (Medical Negligence (Represents Defendants))
  • Recognized in the 2025 edition (and since 2022) of the Canadian Legal Lexpert Directory (Corporate Commercial Litigation)
  • Recognized in the 2022 edition of the Best Lawyers in Canada (Banking and Finance Law)

Client Testimonials

“Greg Fleetwood is very efficient and effective, and he is also a friend.”

- Tom Fulton, Re/Max Performance Realty

“[Greg] is very understanding and supportive.”

- President & Medical Director in the Health Care Industry