Leaf senescence regulates grain yield. However, the modulation of leaf senescence in sorghum under legume-based intercrop systems and nitrogen (N) fertilization is not known. The objective of the study was to investigate the effect of intercropping two sorghum (Gadam and Serena) and cowpea (K80, M66) varieties and sole cropping systems and different fertilizer N rates (0, 40, and 80 kg·N·ha−1) on the time course of postflowering sorghum leaf senescence and understand how senescence modulates grain yield. The experiment was laid out in a randomized complete block design with a split-plot arrangement with three replications. Leaf senescence was assessed from flowering to maturity at (a) whole-plant level by the visual scoring of green leaves and (b) flag leaf scale by measuring leaf greenness with a SPAD 502 chlorophyll meter. A logistic function in SigmaPlot was fitted to estimate four traits of leaf senescence, including minimum and maximum SPAD (SPADmin, SPADmax), time to loss of 50% SPADmax (EC50), and the rate of senescence. Irrespective of the cowpea variety, intercropping reduced sorghum grain yield by 50%. The addition of N increased yield by 27% but no effect was detected between 40 and 80 kg·N ha−1. Intercropping delayed leaf senescence at the whole plant by 0.2 leaves plant−1 day−1 but reduced SPADmax of the flag by 8 SPAD units and rate of senescence by 4 SPAD units day−1 compared with sole crop system. Fertilizer N delayed leaf senescence (
P
≤
0.05
) at whole-plant and flag leaf scales. Cropping System × nitrogen modulated senescence at whole-plant and flag leaf scales and sorghum grain yield but marginally influenced other traits. While EC50 did not correlate with grain yield, faster rates of senescence and leaf greenness were associated with high yield under the sole crop system. Overall, N was the main factor in driving sorghum leaf senescence while the intercropping effect on senescence was nonfunctional. Effects of competition in sorghum-legume intercropping and source-sink relationships on the patterns of leaf senescence deserve further investigation.