This paper uses the industry of origin approach to analyze value added and labor productivity outcomes arising from progressive liberalization of government and from statutory board control of transport and communications in Singapore. The paper compares these outcomes with those from the market-orientated, more privatized transport and communications sector in Hong Kong, for the benchmark year 2004 and a review period from 1990 to 2005. The study is among the first to carefully compare labor productivity in specific sectors between the two countries. Although Singapore generally recorded higher levels of labor productivity, there was some catch-up by Hong Kong in the later part of the review period. There was also substantial variation in labor productivity performance within sectoral branches in the two sectors. The study suggests there is some evidence that the different political-economic structures and policy approaches to deregulation and liberalization played a role in determining productivity performance in the transport and communications sectors in Singapore and Hong Kong. The analysis infers a potential, increasing focus on privatization as the driving force for further liberalization of the transport and communications sector in Singapore.