Building upon the circumplex approach to (de)motivating styles defined by self-determination theory, this research aimed: (a) to analyse the extent to which physical education (PE) teachers’ (de)motivating teaching approaches differ across gender, school level, and years of teaching experience, and (b) to test paths from PE teachers’ need-based experiences to their (de)motivating teaching approaches, via motivation quality. A purposive and cross-sectional sample of 667 Spanish PE teachers (63.7% male; 54.7% primary; mean teaching experience = 10.77 years) participated. The overall results found that male, secondary school, and more experienced teachers scored lower on autonomy-supportive approaches, and higher on controlling and chaotic approaches. The findings also showed that, after controlling for gender, school level, and teaching experience, need satisfaction showed a direct significant effect on autonomous motivation and an indirect effect on participative, attuning, guiding, and clarifying approaches via autonomous motivation. Need frustration showed a direct significant effect on controlled motivation and amotivation and an indirect effect on demanding, domineering, abandoning, and awaiting approaches via controlled motivation and amotivation. Another noteworthy result is the positive relationship between need satisfaction and controlled motivation. Our results underscore the role that PE teachers’ personal traits play in the adaptive motivational mechanisms underlying their variety of (de)motivating approaches to PE teaching.