Space-based cropland phenology monitoring substantially assists agricultural managing practices and plays an important role in crop yield predictions. Multitemporal satellite observations allow analyzing vegetation seasonal dynamics over large areas by using vegetation indices or by deriving biophysical variables. The Nile Delta represents about half of all agricultural lands of Egypt. In this region, intensifying farming systems are predominant and multi-cropping rotations schemes are increasing, requiring a high temporal and spatial resolution monitoring for capturing successive crop growth cycles. This study presents a workflow for cropland phenology characterization and mapping based on time series of green Leaf Area Index (LAI) generated from NASA’s Harmonized Landsat 8 (L8) and Sentinel-2 (S2) surface reflectance dataset from 2016 to 2019. LAI time series were processed for each satellite dataset, which were used separately and combined to identify seasonal dynamics for a selection of crop types (wheat, clover, maize and rice). For the combination of L8 with S2 LAI products, we proposed two time series smoothing and fitting methods: (1) the Savitzky–Golay (SG) filter and (2) the Gaussian Processes Regression (GPR) fitting function. Single-sensor and L8-S2 combined LAI time series were used for the calculation of key crop Land Surface Phenology (LSP) metrics (start of season, end of season, length of season), whereby the detection of cropland growing seasons was based on two established threshold methods, i.e., a seasonal or a relative amplitude value. Overall, the developed phenology extraction scheme enabled identifying up to two successive crop cycles within a year, with a superior performance observed for the seasonal than for the relative threshold method, in terms of consistency and cropland season detection capability. Differences between the time series collections were analyzed by comparing the phenology metrics per crop type and year. Results suggest that L8-S2 combined LAI data streams with GPR led to a more precise detection of the start and end of growing seasons for most crop types, reaching an overall detection of 74% over the total planted crops versus 69% with S2 and 63% with L8 alone. Finally, the phenology mapping allowed us to evaluate the spatial and temporal evolution of the croplands over the agroecosystem in the Nile Delta.