Understanding which trees farmers prefer, what determines their survival and enhancing farmer knowledge of tree management is key to increasing tree cover in agricultural landscapes. This article presents data on tree seedling survival under different tree planting and management practices in Kenya and Ethiopia. Data were collected from 1600 households across three Counties in Kenya and 173 households across four Woredas in Ethiopia, using a structured questionnaire which was administered through the Open Data Kit. Data on seedling survival were collected at least six months after tree seedlings were planted. To understand how planting and management practices influence tree planting across the different socioeconomic and biophysical contexts, both household level and individual tree level data were collected. Household level data included socio-economic and biophysical characteristics of the households while tree specific data included when the tree seedling was planted, where it was planted, the management practices employed and whether surviving. The datasets described in this article help understand which options confer the best chance survival for the planted seedlings and in which socio-economic and biophysical contexts they are most successful. [Abstract copyright: © 2021 The Author(s). Published by Elsevier Inc.]