The aim of this study was to investigate the complex relationship between students' mathematics confidence, confidence with technology, attitude to learning mathematics with technology, affective engagement and behavioural engagement, achievement, gender and year level. The participants were secondary students from state co-educational schools in Metropolitan Athens, Greece. Gender differences as well as differences between year levels and the resulting clusters of students were investigated by using a MANOVA. It was found that boys expressed more positive views towards mathematics and more positive views towards the use of technology in mathematics, compared to girls. It was also found that high achievement in mathematics was associated with high levels of mathematics confidence, strongly positive levels of affective engagement and behavioural engagement, high confidence in using technology and a strongly positive attitude to learning mathematics with technology. Low levels of mathematics achievement was associated with low levels of mathematics confidence, strongly negative levels of affective engagement and behavioural engagement, low confidence in using technology, and a negative attitude to learning mathematics with technology. (Contains 2 figures and 4 tables.)