The present study investigates the competencies and opinions of pre-service English language teachers on the usability of web 2.0 tools in measuring English speaking skills. To this aim, an experimental study involving both qualitative and quantitative data tools was designed. The questionnaire was applied as a pre-test and post- data. In the quantitative phase, Vogt and Tsagari (2014)'s LAL questionnaire was adapted and used to collect data. In the qualitative phase, an open-ended written interview consisting of five questions was applied to collect the qualitative data of the study. The participants of the study are senior students studying in the English language teaching program at a state university in Turkey. The findings show that the participants initially felt not competent enough and needed training in online speaking skills assessment. However, the post test results revealed that the six weeks treatment contributed to their competency, literacy, and training needs levels in respect to digital speaking assessment. Moreover, most of the participants had positive perceptions towards web 2.0 tools and online speaking skills assessment. In addition to the findings, limitations of the study and suggestions for further studies were presented.