Pasture management is highly dependent on accurate biomass estimation. Usually, such activity is neglected as current methods are time-consuming and frequently perceived as inaccurate. Conversely, spectral data is a promising technique to automate and improve the accuracy and precision of estimates. Historically, spectral vegetation indices have been widely adopted and large numbers have been proposed. The selection of the optimal index or satisfactory subset of indices to accurately estimate biomass is not trivial and can influence the design of new sensors. This study aimed to compare a canopy-based technique (rising plate meter) with spectral vegetation indices. It examined 97 vegetation indices and 11,026 combinations of normalized ratio indices paired with different regression techniques on 900 pasture biomass data points of perennial ryegrass (Lolium perenne) collected throughout a 1-year period. The analyses demonstrated that the canopy-based technique is superior to the standard normalized difference vegetation index (∆, 115.1 kg DM ha−1 RMSE), equivalent to the best performing normalized ratio index and less accurate than four selected vegetation indices deployed with different regression techniques (maximum ∆, 231.1 kg DM ha−1). When employing the four selected vegetation indices, random forests was the best performing regression technique, followed by support vector machines, multivariate adaptive regression splines and linear regression. Estimate precision was improved through model stacking. In summary, this study demonstrated a series of achievable improvements in both accuracy and precision of pasture biomass estimation, while comparing different numbers of inputs and regression techniques and providing a benchmark against standard techniques of precision agriculture and pasture management.