The relationship between the early ground cover and the grain yield in winter wheat is not yet fully understood. In a winter wheat breeding programme, selection for early ground cover is traditionally made using visual scoring. Although visual scoring is preferred as a phenotypic screening tool by wheat breeders, its output may not be reliable, as it requires experience. A smartphone camera-based digital image technique can be recommended as a feasible, reliable, repeatable, affordable, and fast selection tool for early ground cover in wheat as an alternative to visual scoring. For this purpose, two wheat trials were conducted in the 2017–2018 and 2019–2020 seasons. In both seasons, 215 wheat genotypes in total, together with three checks from spring wheat, were tested under rain-fed conditions in the spring wheat zone in Turkey. All the tested wheat genotypes were grouped into spring, facultative, and winter growth habit using visual scoring. Simultaneously, photos were taken from each plot with a smartphone camera, and the early ground cover (%) was estimated using the smartphone camera-based digital image technique. The relationships between grain yield, visual scoring, and early ground cover could so be estimated. In both seasons, significant negative correlation between grain yield and visual scoring (r = −0.679** and r = −0.704**, respectively) and significant positive correlation between the grain yield and the early ground cover (r = 0.745** and r = 0.747**, respectively) were observed. The correlation between visual scoring and early ground cover were negative (r = −0.862** and r = −0.926**, respectively). The broad sense heritability estimates in both seasons were 0.51 and 0.85, respectively, for early ground cover, 0.91 and 0.94 for visual scoring, and 0.86 and 0.69 for grain yield. In this study, we revealed that testing winter wheat genotypes in the spring wheat zone rather than in the winter wheat zone could be a more effective way to unveil the positive relationship between the early ground cover and the grain yield. We have shown that the smartphone-based digital image technique is a useful selection tool for early ground cover in winter wheat.