Grass-based suckling beef-derived foods occasionally exceed regulatory levels for polychlorinated biphenyls (PCBs) and dibenzo-p-dioxins/dibenzofurans (PCDD/Fs). Ensuring chemical safety requires understanding the cow-calf transgenerational PCB and PCDD/F fate. The current focus was on dairy cows, omitting transgenerational fate and suckling beef-related physiological effects. This study aimed to investigate PCB and PCDD/F absorption, distribution, metabolism, and excretion within 12 Simmental cows (six primiparous/six multiparous) and 12 calves fed with the milk of their respective mothers for 109 days prepartum until 288 days in milk (DIM), i.e., slaughter time. Eight cows were exposed to a grass silage-soil mixture. Four were decontaminated after DIM164 by receiving uncontaminated grass silage, which four control cows received. An input-output balance during gestation and lactation was computed from PCB, PCDD/F, and lipid inputs (solid feed/milk intakes), outputs (fecal/milk excretions), and body storage (initial/final burdens). At slaughter, PCB and PCDD/F tissue distribution, and lipid allometry were linked. Apparent PCB and PCDD/F absorption rates and metabolized fractions decreased with increasing chlorination. In calves, PCB absorption showed no effect due to chlorination (steady range: 71–87%). High-chlorinated PCB and PCDD/F absorption rates decreased when provided through soil. Cows excreted PCBs and PCDD/Fs via feces (50% relative to input) and milk (9%) and accumulated only 5% in their body, whereas calves accumulated the largest fraction of the total input in their bodies (44%). Cow physiology affected accumulation and excretion, as in primiparous cows, net body burden and milk assimilation efficiencies were higher and lower, respectively, than in multiparous. Liver-specific enrichment was observed in cows and calves (7.0- and 3.2-fold iPCB and dlPCB + PCDD/F TEQ, compared to empty body-based lipid concentrations), whereas iPCBs were also enriched in kidneys (3.1-fold) and muscles (1.5-fold). Consequently, adipose concentrations did not perfectly represent most edible beef tissues. This highlights the essence of integrating the interplay between physicochemical pollutant properties and animal physiology in transgenerational transfer assessments of PCBs and PCDD/Fs.