Fertility-induced performance alterations in wheat (cv. Kalyansona) were evaluated under 2 cycles of droughts at various developmental stages, and also under repeated droughts. The significant alleviation of growth and yield, despite the higher stress experienced by plants under improved soil fertility, seems to be related to larger root growth and greater post-drought nutrient uptake and not to favorable tissue water modulations. Limited wet-period interludes, under repeated stress, reduced these advantages. Stress-mediated increases in proline and free amino acids and the decline in chlorophyll content in leaves followed established trends. Their levels were relatively higher under better soil fertility. The proline accumulation was reduced in the 2nd cycle of drought, as compared to the 1st, indicating an absence of hardening effect.