Holly Cunliffe Associate

Speaks:  English

Year of Call: 2014 - Ontario

Primary phone: +1 416-862-3629

Fax: +1 416-862-7661

Email: holly.cunliffe@gowlingwlg.com

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Primary office:  Toronto

Holly Cunliffe

Holly Cunliffe is a litigation lawyer in Gowling WLG's Private Client Services Group. Holly represents individuals, trust companies and fiduciaries with litigious estate, trust and capacity matters. She is preferred counsel for LawPRO on matters of professional negligence with respect to estate and trust issues, and sits on the executive committee for the Ontario Bar Association’s Elder Law section.

Harnessing her broad experience in this complex and highly emotionally charged area of the law, Holly seeks to resolve estate, trust and capacity disputes efficiently and with compassion. Holly assists clients with a range of court proceedings, such as will challenges, applications to pass attorney and trustee accounts, dependent support claims, rectification and interpretation of wills and trusts, variations of trust deeds, power of attorney and capacity disputes, estate and trust administration issues, trustee applications for advice and directions, appointment or removal of trustees/guardians, breaches of trust, and guardianships.

Prior to joining Gowling WLG, Holly practised at a large international full-service law firm where she represented clients in commercial litigation disputes, in addition to estate/trust litigation. She brings valuable insight having represented clients in matters involving civil fraud, asset and debt recovery, real estate disputes, contract disputes, oppression actions, civil enforcement, employment disputes, product liability, judicial reviews and Indigenous law.

Holly has acted as counsel before the Ontario Superior Court of Justice (including the Estates and Commercial Lists), Court of Appeal for Ontario, Ontario Court of Justice and Ontario Small Claims Court. She is currently studying for her Trust and Estate Practitioner (TEP) designation.

Holly is a regular volunteer with the Pro Bono Ontario Duty Counsel Project (Small Claims Court) where she has donated her time since 2012, assisting low-income parties with their civil litigation matters including representation at settlement conferences and trial. Holly also volunteers with the Pro Bono Ontario Free Legal Advice Hotline, providing advice on estates, powers of attorney, civil litigation, and civil appeals to low income clients.  Holly also acts as a mentor to students of the Western Business Law Clinic, which provides pro bono legal counsel to small startup businesses and aspiring entrepreneurs who cannot afford legal counsel.

Career & Recognition

Filter timeline:
  • 2018

    • Education
      39th Annual Osgoode Hall Intensive Trial Advocacy Workshop
    • Community
      Western Business Law Clinic (Mentor)
  • 2017

    • Education
      The Society of Trust and Estate Practitioners (STEP) – diploma student (in progress)
  • 2014

    • Community
      Law in Action Within Schools
    • Qualifications (Year of Call/Admission, etc.)
      Year of Call, Ontario
    • Community
      Pro Bono Law Ontario Small Claims Court Duty Counsel Project, Toronto
  • 2013

    • Education
      Western University – JD
  • 2010

    • Community
      Community Legal Services, Western University
    • Community
      Western Business Law Clinic
  • 2007

    • Education
      McGill University – BA


  • Canadian Bar Asssociation
  • Ontario Bar Association (Trusts and Estates Law, Women Lawyers Forum)
  • The Advocates' Society
  • the Society of Trust and Estate Practitioners (STEP)
  • Co-authored Chapter 9 ("Canada") in The International Arbitration Review - Edition 8,  Law Business Research Ltd., August 2017
  • Co-authored with Matthew Fleming, "Employees cannot claim against directors for failing to stop fraud", Legal Alert, Vol.35 no.9, p.65, April 2016
  • Co-authored with Matthew Fleming, "Court of Appeal holds that polluters pay... personally", Legal Alert, Vol.35 no.1, p.6, April 2016
  • Co-authored with Matthew Fleming, "Rahimi decision a welcome one for directors and officers", Legal Alert, Vol.34 no.11, p.85, February 2016
  • Co-authored with Matthew Fleming, "Policy ambiguity resolved in favour of directors and officers", Legal Alert, Vol.34 no.9, p.65, December 2015
  • Co-authored with Matthew Fleming, "Director's estate liable for unpaid wages arising from oppression", Legal Alert, Vol.34 no.5, p.38, August 2015
  • Co-authored with Martha Harrison and Thomas P. O'Leary, Chapter 10 ("Canada") in The International Arbitration Review - Edition 6,  Law Business Research Ltd., June 2015
  • Co-authored with Mathew Fleming, "Director Personally Liable for Arbitration Award," Legal Alert, Vol.34 no.2, p.9, May 2015
  • Co-authored with Matthew Fleming, "Director resignation needs to be effective to avoid liability", Legal Alert, Vol. 33, no.11, February 2015
  • Co-authored with Matthew Fleming, "Ontario Court of Appeal deals blow to securities class actions"International Law Office, February 24, 2015
  • Co-authored with Michael Schafler, "Assumed Jurisdiction in Canada – What Next?"  Delivered at the International Bar Association High Stakes Conference, December 4, 2014
  • Tax Court Interprets “Ownership” for Purposes of GST/HST New Housing RebateCanadian Tax Litigation,  February 12, 2014
  • Taxable in Canada? Not a Black and White SituationCanadian Tax Litigation, January 24, 2014
  • Fiduciary Duty for Investment Dealers and Advisors: The Impact of a Statutory Best Interest Duty on Civil Liability, September 2013

Representative Work



  • Guz v. Olszowka, 2019 ONSC 6441
  • Myer v. Rubin, 2017 CarswellOnt 21960
  • Typhoon Offshore B.V. et al v. Jacob et al, 2017 ONSC 3715
  • Jacob Securities Inc. v. Typhoon Capital B.V., 2016 ONSC 604
  • Bayer Inc. v. Belfield Investment Corp., 2015 ONSC 5029
  • Bayer Inc. v. Belfield Investment Corp., 2015 ONSC 5715
  • Rea v. Wildeboer, 2015 ONCA 373