Perennials can produce more biomass and partially replace annual crops. However, environmental benefits of perennials over annuals in terms of nitrous oxide (N
2O) emissions have rarely been compared in a long-term field experiment. By combining automatic and manual chamber methods, we aimed to develop reliable N
2O estimates from annual and perennial systems. We measured N
2O emissions from: i. perennial grass during renovation including spring barley as catch crop (SB/RG); ii. perennial grass-clover mixture (GC); iii. triticale monoculture (Trit). Results showed that cumulative N
2O emissions from SB/RG were higher than GC or Trit. The highest emission rate was measured for SB/RG (258.9 µg N
2O
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N m
-2 h
-1) after fertilization in spring. Increased N
2O emissions were also seen for a short period after direct grass seeding in August. For Trit, N
2O emissions increased after fertilization in March and ploughing in late September. In GC (fertilized with P and K), there was no N
2O peak after grass cutting. Both from manual and automatic chamber systems, “hot moments” of N
2O emissions contributed ∼16–79 % of cumulative emissions. By predicting hot moments and scheduling frequent measurements, manual chambers captured most of the N
2O dynamics. The results indicated that the hot moments of N
2O emissions were better quantified by automatic chambers, while some of the hot moments, for instance, fertilization and ploughing in Trit were accurately captured with manual chambers. Soil nitrate and ammonium were positively associated with N
2O emissions, whereas biomass N uptake was negatively associated. We conclude that perennial (GC) is a promising system for high biomass production with low environmental impact. Strategies such as growing spring barley as a catch crop, grass seeding with shallow tillage, and fertilization of newly seeded grass matching crop N demand are needed to reduce the higher risk for N losses.