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Doolan v. Revenue Commissioners

16 October 2026 – High Court – [2026] IEHC 682

Case stated from Tax Appeals Commissioner on whether contract for sale of land was ‘conditional’ within section 542(1)(b) of the Taxes Consolidation Act 1997 [1]. Contract signed on 22 December 2015; transfer in 2017 [5]. Appellant needed disposal in 2015 to set loss against 2015 gain on shares [4]. Contract ‘in substance, an option to purchase’ [27]. Determination upheld; all four questions answered in the negative [28].

1. Conditional contract

  1. 1.

    Section 542(1)(b) of the Taxes Consolidation Act 1997, as interpreted by Flaherty v. Revenue Commissioners [2026] IESC 4, applied: “There must be some contractual obligation, but the principal performance will be conditional on some event… And in the context in which s.542(1)(b) is to operate, that principal performance will be the disposition of an asset. There will be a contract, in other words, but no contract imposing obligations on the vendor to sell, or the purchaser to buy the asset until the event specified in the condition has occurred.” [15]

    1. 1.1

      Hatt v. Newman (Inspector of Taxes) [2000] STC 113, as adopted in Flaherty: Section distinguishes “A condition that prevents ‘certain contractual obligations arising when the contract was concluded’ and one that does not.” [14]

    2. 1.2

      Option the paradigm: “the paradigmatic example described in the section – that of the option” [16]

  2. 2.

    Purchaser’s discretion untrammelled: ‘This, on the face of it, gave the purchaser an untrammelled right, at any time prior to 30 June, 2016, to withdraw from the sale.’ [18]

    1. 2.1

      Principal obligation not binding: ‘principal obligation of the purchaser, which was to purchase the property in sale, was not – in substance or in reality – binding on the purchaser until after the purchaser had had an opportunity to investigate the very wide range of matters set out in the special conditions’ [19]

  3. 3.

    Hand v. Greaney [2004] IEHC 391 applied a fortiori: ‘Whereas in Hand v. Greaney, the purchaser had to be happy with the scope and conditions of the planning permission, in this case, the purchaser could elect not to proceed if dissatisfied with anything relating to the property in sale.’ [22]

  4. 4.

    Retention-permission obligation irrelevant: Special Condition 6 and the rest of Special Condition 7 ‘afforded a discretion to the purchaser which went far beyond the question of whether the necessary application for retention permission had been made within the time specified.’ [23]

2. Capacity to contract

  1. 5.

    Camiveo Ltd v. Dunnes Stores [2015] IESC 43, [2015] 2 IR 698 applied: ‘transferee for value enjoys significant rights prior to registration’ [25]

    1. 5.1

      Alternative finding decisive: ‘issue as to the capacity of the vendor to sign a valid contract for sale before he became registered as full owner therefore had no bearing on the correctness of TAC’s central finding that the entire contract was in substance an option to purchase’ [26]

3. Orders

  1. 6.

    Determination upheld: All four questions in the Case Stated answered in the negative [28]. Disposal not deemed made until the condition was satisfied in 2017 [27].