Knowledge of the rock mass strength is important for the design of all types of underground excavations. A frequently applied approach for estimation of the rock mass strength is through an empirical failure criterion, often in conjunction with rock mass classification/characterisation systems. This paper presents a review of existing methods to estimate the rock mass strength using empirical failure criteria and classification/characterisation systems—in this study, commonly denoted as estimation methods. A literature review of existing methods is presented, after which a set of methods were selected for further studies. The selected methods were used in three case studies, to investigate their robustness and quantitatively compare the advantages and disadvantages of each method. A Round Robin test was used in two of the cases. The case studies revealed that the N, Yudhbir-RMR76, RMi, Q-, and Hoek–Brown-GSI methods, appeared to yield a reasonable agreement with the measured strengths. These methods are thus considered the best candidates for realistic strength estimation, provided that care is taken when choosing values for each of the included parameters in each method. This study has also clearly shown the limits of presently available strength estimation methods for rock masses and further work is required to develop more precise, practical, and easy-to-use methods for determining the rock mass strength. This should be based on the mechanical behaviour and characteristics of the rock mass, which implies that parameters that consider the strength of intact rock, block size and shape, joint strength, and physical scale, are required.