I think the Capital contribution route is quite strong - Section 552(2) of the Taxes Consolidation Act states "the amount of any expenditure wholly and exclusively incurred by the person or on the person's behalf for the purpose of purpose of enhancing the value of the asset"..... can be allowed as a deduction from the consideration. I would be of the opinion that a capital contribution would immediately enhance the value of your shares in the company - i.e. because of your capital contribution to the company, the company had more net assets, shares derive their value from the net assets of the company - de facto you capital contribution has increased the value of your shares and can be taken as a deduction in calculating the capital gains tax