Since their recent introduction, conditional random fields (CRFs) have been successfully applied to a multitude of structured labelling tasks in many different domains. Examples include natural language processing (NLP), bioinformatics and computer vision. Within NLP itself we have seen many different application areas, like named entity recognition, shallow parsing, information extraction from research papers and language modelling. Most of this work has demonstrated the need, directly or indirectly, to employ some form of regularisation when applying CRFs in order to overcome the tendency for these models to overfit. To date a popular method for regularising CRFs has been to fit a Gaussian prior distribution over the model parameters. In this thesis we explore other methods of CRF regularisation, investigating their properties and comparing their effectiveness. We apply our ideas to sequence labelling problems in NLP, specifically part-of-speech tagging and named entity recognition. We start with an analysis of conventional approaches to CRF regularisation, and investigate possible extensions to such approaches. In particular, we consider choices of prior distribution other than the Gaussian, including the Laplacian and Hyperbolic; we look at the effect of regularising different features separately, to differing degrees, and explore how we may define an appropriate level of regularisation for each feature; we investigate the effect of allowing the mean of a prior distribution to take on non-zero values; and we look at the impact of relaxing the feature expectation constraints satisfied by a standard CRF, leading to a modified CRF model we call the inequality CRF. Our analysis leads to the general conclusion that although there is some capacity for improvement of conventional regularisation through modification and extension, this is quite limited. Conventional regularisation with a prior is in general hampered by the need to fit a hyperparameter or set of hyperparameters, which can be an expensive process. We then approach the CRF overfitting problem from a different perspective. Specifically, we introduce a form of CRF ensemble called a logarithmic opinion pool (LOP), where CRF distributions are combined under a weighted product. We show how a LOP has theoretical properties which provide a framework for designing new overfitting reduction schemes in terms of diverse models, and demonstrate how such diverse models may be constructed in a number of different ways. Specifically, we show that by constructing CRF models from manually crafted partitions of a feature set and combining them with equal weight under a LOP, we may obtain an ensemble that significantly outperforms a standard CRF trained on the entire feature set, and is competitive in performance to a standard CRF regularised with a Gaussian prior. The great advantage of LOP approach is that, unlike the Gaussian prior method, it does not require us to search a hyperparameter space. Having demonstrated the success of LOPs in the simple case, we then move on to consider more complex uses of the framework. In particular, we investigate whether it is possible to further improve the LOP ensemble by allowing parameters in different models to interact during training in such a way that diversity between the models is encouraged. Lastly, we show how the LOP approach may be used as a remedy for a problem that standard CRFs can sometimes suffer. In certain situations, negative effects may be introduced to a CRF by the inclusion of highly discriminative features. An example of this is provided by gazetteer features, which encode a word's presence in a gazetteer. We show how LOPs may be used to reduce these negative effects, and so provide some insight into how gazetteer features may be more effectively handled in CRFs, and log-linear models in general.