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The construction sector in Swaziland is not only a significant source of direct employment but also a sector which contributes, through its wide range of projects and operations. The Swazi economy is unable to deliver employment for a growing number of workers. Structural unemployment and poverty are persistent and growing problems in contemporary Swaziland. Small businesses have been advocated as an important means of generating employment in which Swaziland is not an exception. The paper first outlined the arguments that have been put forward for the development of small contractors in the construction sector in sub-Saharan Africa. Secondly, the paper described the problems and successes that have been experienced in Swaziland in relation to small contractor development programme. The lastly, the paper concluded with recommendations for the future which will enhance the success of small and medium size contractors in Swaziland.