Sentiment analysis has emerged as a field that has attracted a significant amount of attention since it has a wide variety of applications that could benefit from its results, such as news analytics, marketing, question answering, knowledge management and so on. This area, however, is still early in its development where urgent improvements are required on many issues, particularly on the performance of sentiment classification. In this thesis, three key challenging issues affecting sentiment classification are outlined and innovative ways of addressing these issues are presented. First, text pre-processing has been found crucial on the sentiment classification performance. Consequently, a combination of several existing preprocessing methods is proposed for the sentiment classification process. Second, text properties of financial news are utilised to build models to predict sentiment. Two different models are proposed, one that uses financial events to predict financial news sentiment, and the other uses a new interesting perspective that considers the opinion reader view, as opposed to the classic approach that examines the opinion holder view. A new method to capture the reader sentiment is suggested. Third, one characteristic of financial news is that it stretches over a number of domains, and it is very challenging to infer sentiment between different domains. Various approaches for cross-domain sentiment analysis have been proposed and critically evaluated.