Musicians face challenges when using stereo headphones to perform with one another, due to a lack of audio intelligibility and the loss of their usual benchmarks. Also, high levels of click tracks in headphone mixes hinder performance subtleties and harm performers’ aural health. This chapter discusses the approaches and outcomes of eight case studies in professional situations that aimed at comparing the experiences of orchestra conductors and instrumentalists while monitoring their performances through binaural versus stereo headphones. These studies assessed three solutions combining augmented and mixed reality technologies that include binaural with head tracking to conduct a large film-scoring orchestra and jazz symphonic with a click track; binaural without head tracking to improvise in trio or on previously recorded takes in the studio; and active binaural headphones to record diverse genres on a click track or soundtrack. Findings concur to show that better audio intelligibility and recreated natural-sounding acoustics through binaural rendering enhance performers’ listening comfort, perception of a realistic auditory image, and musical expression and creativity by increasing their feeling of immersion. Findings also demonstrate that the reduction of source masking effects in binaural versus stereo headphone mixes enables performers to monitor less click track, and therefore protect their creative experience and aural health.