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Orlando Holloway

Call 2004
Telephone 020 7831 0222
Email orlando.holloway@42br.com


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"An outstanding junior who is excellent with clients." Legal 500 2021

Legal 500

Orlando is an experienced practitioner specialising in Employment, Clinical Negligence and Personal Injury. He represents clients in the Employment Tribunal, High Court and County Court and various appellate courts and is often commended for being approachable, pragmatic, and commercially minded. He has a particular focus on working collaboratively with professional and lay clients.

Orlando has, for a number of years, been ranked as a leading junior in Chambers & Partners (Employment Law).

Orlando is a contributor to Westlaw’s Insight series and gives seminars and training on Employment, Clinical Negligence and Personal Injury issues on a regular basis.



  • “Very personable, well prepared and responsive.” “Very client-friendly.” Chambers & Partners 2019

  • ‘He is very commercial and easy to get along with.’ Legal 500 2018

Ranked in UK Bar Chambers 2019     Legal 500 logo

Selected cases

  • Lozaique v Tesco Stores Ltd UKEAT/0261/18/LA - Representing the Respondent in the EAT responding to the Claimant’s appeal against the Tribunal’s finding that the Claimant’s longstanding overtime rate for guaranteed overtime had been amended by collective bargaining agreements incorporated into his contract of employment.
  • Q v P - Representing the Claimant in a PI claim that settled for £2.5m (at a second JSM). The Claimant was a motorcyclist who developed compartment syndrome, DVT, and then post thrombotic syndrome after he fractured his leg in an accident. The case turned on whether it would be beneficial for the Claimant to have an above knee amputation or whether the usual benefits would be negated by the Claimant’s post thrombotic syndrome.
  • K v S (2018) - Representing the Respondent at a 10 day Employment Tribunal hearing of C’s claims under the Equality Act (Disability, Race, and Religion) and Constructive Unfair Dismissal. The trial was complicated by a number of adjustments required by C as a result of her disability.
  • Re S - Representing an NHS Foundation Trust at a 6 week inquest into the death of a prison inmate as a result of various acts of deliberate self-harm. Orlando’s client was responsible for the provision of mental health services at the prison in question.
  • Drake v Ipsos Mori Ltd [2012] I.R.L.R 973 - Representing the Respondent in the EAT responding to an appeal against the Tribunal’s finding that the Claimant was not an employee. The case turned on whether there was mutuality of obligation where a contract was terminable at will.
  • Re P v CICAP - Acting for a teenaged applicant before the Criminal Injuries Compensation Appeals Panel.
  • P had sustained severe brain damage at the age of 6 weeks when being cared for by her father. After a series of hearings the CICAP accepted that P had been the victim of crime (contradicting the decision made by the police at the time the injury was sustained) and she therefore succeeded in obtaining compensation under the scheme (it being anticipated that she would receive the maximum award of £500,000).
  • Mitie v Imbrahim UKEAT/0067/10/ZT - Advising and representing Mitie in their successful appeal of the tribunal’s decision at first instance that there had been a dismissal of a security officer as a result of a lapse in time between the offer of work following an earlier client request for removal from site.
  • Austin v Tesco Stores Ltd UKEAT/0022/09/MAA - Representing the Respondent in an appeal against the employment tribunal’s finding that A’s dismissal had been fair notwithstanding some procedural irregularities.


  • 2004 Bar Vocational Course
  • 2003 Exeter University LLB

Other information

Away from work Orlando is a keen (but useless) sportsman, an enthusiastic cook, a novice gardener, and an embarrassing Dad.  

News & events

News & events