This paper presents a continental-scale phenological analysis of African savannas and woodlands. We apply an array of synergistic vegetation and hydrological data records from satellite remote sensing and model simulations to explore the influence of rainy season timing and duration on regional land surface phenology and ecosystem structure. We find that (i) the rainy season onset precedes and is an effective predictor of the growing season onset in African grasslands. (ii) African woodlands generally have early green-up before rainy season onset and have a variable delayed senescence period after the rainy season, with this delay correlated nonlinearly with tree fraction. These woodland responses suggest their complex water use mechanisms (either from potential groundwater use by relatively deep roots or stem-water reserve) to maintain dry season activity. (iii) We empirically find that the rainy season length has strong nonlinear impacts on tree fractional cover in the annual rainfall range from 600 to 1800mm/yr, which may lend some support to the previous modeling study that given the same amount of total rainfall to the tree fraction may first increase with the lengthening of rainy season until reaching an "optimal rainy season length," after which tree fraction decreases with the further lengthening of rainy season. This nonlinear response is resulted from compound mechanisms of hydrological cycle, fire, and other factors. We conclude that African savannas and deciduous woodlands have distinctive responses in their phenology and ecosystem functioning to rainy season. Further research is needed to address interaction between groundwater and tropical woodland as well as to explicitly consider the ecological significance of rainy season length under climate change.