The world of work in the United Kingdom has for many years been characterised by major inequalities. Despite hosting some of the world’s highest executive salaries, basic employment and welfare standards tend to be relatively low. Moreover, a series of qualitative shifts in the labour market, in worker protections and in the nature of work have tended both to reproduce and to feed off workers’ unequal socio-economic position. A key causal factor is the ‘perforated’ industrial relations model caused by two generations of trade union decline. This has facilitated a specific mode of labour market flexibility, which is strongly biased towards employer short-term interests and militates against both longer-term employer security needs (for example, to underpin skill investment) and the kinds of flexibilities that might meet worker needs (for example, flexible careers and working time). This chapter investigates the relationship between inequalities and industrial relations and explores positive and negative outcomes via two case studies.