A two-year farm system study was conducted at Canterbury, New Zealand to evaluate the effects on farm productivity, profitability, and nitrogen (N) losses of integrating plantain (Plantago lanceolate L.) and Italian ryegrass (Lolium multiflorum Lam.) into a ryegrass and white clover (RGWC)-based dairy system. Three farm systems were compared: (1) a lower input RGWC-based system (LIRG) with stocking rate of 3.5 cow/ha, annual N fertiliser rate of 150 kg/ha, and imported feed level of <1.2 t DM/cow/year; (2) a lower input ryegrass + plantain-based system (LIRG + PL) with a stocking rate of 3.5 cow/ha, annual N fertiliser rate of 150 kg/ha, and imported feed level of <1.2 t DM/cow/year; and (3) a higher input RGWC-based system (HIRG) with a stocking rate of 5.0 cow/ha, annual N fertiliser rate of 300 kg/ha, and imported feed level of >1.2 t DM/cow/year. Cows in the LIRG + PL system grazed a diverse mix of Italian ryegrass, perennial ryegrass, white clover, and plantain (60% of farmlet area), and a mixed sward of plantain–white clover (40% of farmlet area). The average annual herbage harvested was similar between LIRG + PL and LIRG (11.7 t DM/ha), but greater in HIRG (12.7 t DM/ha) with the increased N fertiliser rate. During the calving to dry-off period, the average imported supplement feed per ha was higher in HIRG (8.0 t DM) compared with LIRG (3.2 t DM) and LIRG + PL (3.7 t DM). Average milk solid production (MS; fat + protein) was similar in LIRG + PL (1640 kg/ha) and LIRG (1622 kg/ha), but greater in HIRG (2130 kg/ha). Estimated profitability (NZD/ha) at milk price of NZD 6.5/kg MS was 10% greater for HIRG than LIRG + PL and LIRG, and similar (<1.5% numerical difference) between LIRG + PL and LIRG. The average estimated annual N leaching loss from the LIRG and LIRG + PL was 31% and 56% less than the loss from the HIRG. These large reductions in N leaching loss were achieved without a large decrease in profitability (i.e., LIRG and LIRG + PL compared to HIRG). In addition, the estimated reduction in N losses from the LIRG + PL system compared to LIRG suggests that an Italian ryegrass + plantain-based dairy system is a viable strategy to reduce the environmental footprint while maintaining farm profitability. However, the environmental benefits of plantain and Italian ryegrass estimated in this study require further confirmation through direct measurements at full farm level.