The increasing interest in the potential use of fiscal incentives as a mechanism for stimulating urban renewal has been highlighted by a number of influential policy sources. This paper assesses the application and outcomes of tax-based incentives in urban regeneration, with particular focus upon the differing models represented by Dublin (Ireland) and Chicago (USA). Issues considered include utilisation of tax incentives, drawing-down of benefits, role of actor groups, ability to lever private-sector finance, impact on property market performance and wider economic influences. Conclusions advance the case for tax-based mechanisms as an instrument in the delivery of urban regeneration but stress the need for complementary structures to exploit fully the fiscal incentives.