Simple Summary The use of 'in paddock' walk-over-weighing scales (WOW) enables cattle liveweight (LW) data collection, remotely and individually, at a high frequency (e.g., daily). Liveweight data obtained can be used to calculate the liveweight change experienced by a dam at calving (Delta LWC), which is linked with calf birth weight (CBW). This study utilised WOW technology to investigate the degree of association between CBW, LW before and after calving, Delta LWC, and cow non-foetal weight loss at calving (NFW) (Delta LWC-CBW = NFW, e.g., membranes, fluids). Such outcomes could contribute to predicting CBW by assessing Delta LWC without the need of weighing the calf manually, which can be a labour and time-consuming operation in the extensive conditions of beef production. There was no correlation between CBW and the LW of the dam before and after calving; however, positive associations between CBW, Delta LWC, and NFW were found. Particularly, 56% of the variation in Delta LWC was attributed to CBW. These findings suggest that the remote monitoring of Delta LWC has potential to be used for CBW predictions, regardless of the LW of the dam around calving time. The present study aimed to develop predictive models of calf birth weight (CBW) from liveweight (LW) data collected remotely and individually using an automated in-paddock walk-over-weighing scale (WOW). Twenty-eight multiparous Charolais cows were mated with two Brahman bulls. The WOW was installed at the only watering point to capture LW over five months. Calf birth date and weight were manually recorded, and the liveweight change experienced by a dam at calving (Delta LWC) was calculated as pre-LW minus post-LW calving. Cow non-foetal weight loss at calving (NFW) was calculated as Delta LWC minus CBW. Pearson's correlational analysis and simple linear regressions were used to identify associations between all variables measured. No correlations were found between Delta LWC and pre-LW (p = 0.52), or post-LW (p = 0.14). However, positive associations were observed between Delta LWC and CBW (p < 0.001, R2 = 0.56) and NFW (p < 0.001, R2 = 0.90). Thus, the results suggest that 56% of the variation in Delta LWC is attributed to the calf weight, and consequently could be used as an indicator of CBW. Remote, in-paddock weighing systems have the potential to provide timely and accurate LW data of breeding cows to improve calving management and productivity.