Reliable assessment of crop water stress is essential for improving irrigation efficiency for upland crop and orchard fruit production. Thermal sensing combined with the crop water stress index (CWSI) provides a non-destructive approach for characterizing plant water status; however, its performance depends strongly on baseline determination, sensing platform, canopy architecture, environmental conditions, image-processing procedures, and validation strategy. This paper aimed to review thermal imaging and point-based infrared thermometry (IRT) approaches for CWSI measurement and mapping, with particular emphasis on sensing requirements of upland field crops and orchard fruit tree canopies. A PRISMA-aligned literature search was conducted using major scientific databases and complementary citation tracking, resulting in 68 primary studies included in the structured thematic synthesis. Empirical, theoretical, and artificial-reference CWSI formulations were compared together with handheld, ground-based, unmanned aerial vehicle (UAV)-mounted, fixed camera, and point-based IRT sensing configurations. Radiometric calibration, canopy segmentation, temperature extraction, spatial interpolation, and physiological validation methods were critically evaluated. The reviewed evidence indicates that image-based approaches provide valuable spatial information but remain sensitive to radiometric drift, mixed canopy–background pixels, shadowing, and baseline uncertainty, whereas point-based IRT offers high temporal resolution but depends strongly on representative sensor placement and field-of-view geometry. These limitations differed according to canopy architecture, with soil–background contamination being particularly important in incomplete field canopies and radiation-driven within-canopy heterogeneity being more important in orchards. Combining periodic spatial thermal mapping with continuous point-based monitoring provided a promising framework for precision irrigation. Future research should prioritize transferable baseline parameterization, standardized uncertainty reporting, multi-season commercial validation, benchmark datasets, and crop-specific irrigation thresholds.