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Despite some recent successes in deciphering new cancer molecular makers, there is still a clear and continual need to develop new technologies that help characterizing existing biomarkers or facilitate discovery of new biomarkers. An important systems biology opportunity on this respect is provided by understanding the glycosylation changes associated with cancer. Indeed, interest in cancer glycosylation has expanded over the past decade and large amount of data relevant to cancer glycosylation has been accumulating rapidly. Furthermore, new and improved sophisticated glycoinformatics tools, methods and databases for glycan analysis now offer the opportunity to investigate this data for understanding the role that glycans play in cancer glycosylation. Here we summarize developments of glycoinformatics tools to support analysis of cancer glycosylation and experimental glycoproteomics approaches. In addition, we discuss challenges faced by glycoinformatics for the integration and interrogation of disparate high-throughput glycan data sets in order to assimilate technologies and better address cancer glycosylation. We also provide examples of integrative glycoinformatics approaches that lead to a better understanding of cancer glycosylation as a complex cellular process.