Improved pass accuracy is a prominent determinant of success in football. It demands an effective interaction of complex behavioral and cortical dynamics. Exploring differences in the ability to sustain an accurate pass behavior in a stable setting and the associated cortical dynamics at different expertise levels may provide an insight into skilled strategies contributing to superior accuracy in football. The aim of this study is to compare trial-to-trial variability of pass biomechanics and the corresponding cortical dynamics during short-distance passes between novices and experienced football players. Thirty participants (15 novices, 15 football players) performed 90 short-distance passes. The intertrial variability of pass biomechanics (foot acceleration, range of hip flexion, knee flexion and foot rotation) was assessed by means of multiscale entropy. The task-related cortical dynamics were analyzed via source-derived event-related spectral perturbations. Experienced players demonstrated higher accuracy and overall lower entropy values across multiple time scales which was significant for hip flexion. The electroencephalography data revealed group differences in parieto-occipital alpha desynchronization and frontal theta synchronization in successive phases of passes. The current findings suggest that experienced football players may show a skilled ability to recruit and retain pass biomechanics promoting higher accuracy, whereas novices may show an explorative behavior with higher spatial variability. This difference may be associated with distinctive visuospatial and attentional strategies acquired with expertise in football. Our study provides an insight into expertise-specific behavioral and cortical dynamics of superior accuracy in football and a basis for its prospective investigation in enriched contexts.