This paper seeks to build on and provide empirical evidence concerning a: over the long term, in most of tropical Asia and Southeast Asia, it is not large farms that replace small ones, since, on the contrary, what is clearly occurring is a transition from plantation to smallholders for an important number of cash crops. Then why is this recent surge in large-scale land acquisitions occurring? To examine this issue, we seek to bridge the recent literature on land grabbing with the long-established debate on the relation between large and small farms. For this, we intend to investigate historical transformation of perennial tree crop production in Malaysia and Indonesia, two dominant cash crop producers. To do so, we focus on two important sectors, rubber and palm oil, both major cash crops in those countries, for which smallholders claim a large share of ownership. First, we briefly revisit discussions on the relation between large and small farms to identify key issues in the debate in lieu of conceptual framework. Second, with regard to the cultivation of rubber in Malaysia and Indonesia, we provide a historical perspective on the institutional and economic contexts which defined the relation between small and large farms. Third, for comparative purposes, we attend to the more recent expansion of oil palm in the region involving the emergence of smallholdings. For both crops, we are paying particular attention to national agricultural policies and context that favoured the consolidation and development of smallholder plantation agriculture. Finally and more generally, we discuss the issue of labour and employment.