Instrumented mouthguard (iMG) sensors have been developed to measure sports head acceleration events (HAE) in brain injury research. Laboratory validation studies show that effective coupling of iMGs with the human skull is crucial for accurate head kinematics measurements. However, iMG-skull coupling has not been investigated in on-field sports settings. The objective of this study was to assess on-field iMG coupling using infrared proximity sensing and to investigate coupling effects on kinematics signal characteristics. Forty-two university-level men’s ice hockey (n = 21) and women’s rugby (n = 21) athletes participated in the study, wearing iMGs during 6–7 month in-season periods. Proximity data classified video-verified HAE recordings into four main iMG coupling categories:​ coupled (on-teeth), decoupling (on-teeth to off-teeth), recoupling (off-teeth to on-teeth) and decoupled (off-teeth). Poorly-coupled HAEs showed significantly higher peak angular acceleration amplitudes and greater signal power in medium–high frequency bands compared with well-coupled HAEs, indicating potential iMG movements independent of the skull. Further, even video-verified true positives included poorly-coupled HAEs, and iMG coupling patterns varied between the men’s hockey and women’s rugby teams. Our findings show the potential of using proximity sensing in iMGs to identify poorly-coupled HAEs. Utilizing this data screening process in conjunction with video review may mitigate a key source of sensor noise and enhance the overall quality of on-field sports HAE datasets.