Incorporating plantain with perennial ryegrass and white clover (RGWC) can improve the quality and quantity of grazing pastures; however, the sowing rate could affect the persistence of plantain, pasture yield, and nutritive value in different seasons. The objective of this study was to evaluate the effect of increasing sowing rates of plantain when established with RGWC on the dry matter (DM) yield, botanical composition, nutritive value, and bioactive compounds of the pasture over the first two years after sowing; and to determine the relationship between plantain content and nutritive characteristics in different seasons. The pasture treatments were RGWC, RGWC + low plantain rate (PLL), RGWC + medium plantain rate (PLM), and RGWC + high plantain rate (PLH). The results showed that annual DM yield was similar between treatments. The average plantain content (including leaves and reproductive stem) was 32, 44, and 48% in PLL, PLM, and PLH, respectively. The plantain composition increased in the first 15 months, then declined rapidly to about 20–30% at day 705 after sowing. Compared with RGWC, the plantain-RGWC pastures (PLL, PLM, PLH) had a higher content of organic matter digestibility (OMD), ash, starch, non-structural carbohydrates (NSC), P, S, Ca, Mg, Na, Cl, Zn, B, Co, aucubin, acteoside, and catalpol, while they contained a lower composition of DM%, acid detergent fibre (ADF), neutral detergent fibre (NDF), crude fat (CF), Fe, and Mn. These differences were linearly associated with the content of plantain leaves in the pasture and were higher in summer and autumn than in spring. In conclusion, incorporating plantain into the RGWC pasture can improve herbage nutritive quality, thus potentially increasing farm productivity and environmental benefits. However, further work is required to investigate management interventions to sustain plantain content beyond two years from sowing.