The modelling of machining processes by means of machine-learning algorithms is still based on principles that are especially adapted to mechanical approaches, in which very few inputs are varied with little repetition of experimental conditions. These principles might not be ideal to achieve accurate machine-learning models and they are certainly not aligned with the practicalities of industrial machining in factories. In this research the effect of a new strategy to improve machine-learning model accuracy is studied: experimental repetition. Tool-life prediction in the face-turning operations of AISI 1045 steel discs, depending on different cooling systems and tool geometries, is selected as a case study. Both the side rake and the relief angles of HSS tools are optimized using the Brandsma facing test under dry, MQL, and flooding conditions. Different machine-learning algorithms, such as regression trees, kNNs, artificial neural networks, and ensembles (bagging and Random Forest) are tested. On the one hand, the results of the study showed that artificial neural networks of Radial Basis Functions presented the highest model accuracy (11.4 mm RMSE), but required a very sensitive and complex tuning process. On the other hand, they demonstrated that ensembles, especially Random Forest, provided models with accuracy in the same range, but with no tuning procedure (12.8 mm RMSE). Secondly, the effect of an increased dataset size, by means of experimental repetition, is evaluated and compared with traditional experimental modelling that used average values. The results showed that some machine-learning techniques, including both ensemble types, significantly improved their accuracy with this strategy, by up to 23%. The results therefore suggested that the use of raw experimental data, rather than their averaged values, can achieve machine-learning models of higher accuracy for tool-wear processes.