Pair housing of pre-weaning dairy calves has previously demonstrated positive impacts on their growth, health and behaviour, but longer-term effects on production are still relatively unknown. This study followed a cohort of 431 Holstein heifers, recruited from a single UK commercial dairy farm, from weaning until either culling or the end of their first lactation. All animals were allocated to either individual or pair housing as a pre-weaning calf. Following weaning, all heifers were similarly managed through group housing, feeding with total mixed rations, the use of automatic heat detection for artificial insemination and weighing every two months until conception. Farm staff identified disease occurrences, which were treated following standard operating procedures. First-lactation monthly milk recording was used to measure milk yields and somatic cell counts. Overall mortality (voluntary and involuntary) was 26.6%, with a decreased hazard of exiting the herd if the heifer was pair housed as a calf (HR 0.70; p = 0.067). The voluntary cull rate was highest in the post-insemination period (13.0%) due to poor fertility. Heifers that were pair housed as calves had significantly increased odds of developing udder health issues as a primiparous cow (OR = 1.93, p = 0.022). Despite this, the 305-day milk yields were not associated with the housing group. However, the total milk produced per calf recruited into the original study was greater for pair-housed compared with individually housed calves (8088 kg vs. 7115 kg; p = 0.071), which is likely due to the significantly higher hazard of individually housed calves exiting the herd prematurely.