Daylight discomfort glare evaluation is important when selecting shading properties. New standards recommend allowable glare frequency limits but do not specify the modeling accuracy required for annual glare risk assessment. Fast simulation tools allow users to perform hourly glare evaluations within minutes. However, reliable evaluation of glare through roller shades requires accurate modeling of their specular and diffuse transmission characteristics, affected by color, materials, and weaving technology. This study presents a systematic comparison between commonly used glare simulation methods against the “ground truth” Radiance ray-tracing tool rpict in terms of hourly daylight glare probability (DGP), hourly vertical illuminance (Ev), and annual visual discomfort frequency. The results are presented for two shade fabrics using light transmission models with and without a peak extraction algorithm (Radiance–aBSDF and Radiance–BSDF) for the specular component. The impact of sky/sun discretization on glare prediction is also discussed. The results show that the Radiance 5–Phase Method (5PM) is superior when modeling direct sunlight and DGP through shades, while other investigated methods (3–Phase Method, imageless DGP, ClimateStudio Annual Glare) are not as robust for that purpose. Users are encouraged to understand the underlying assumptions in the imageless methods to avoid errors when simulating glare, especially due to the contrast effects.