Obstructive sleep apnea (OSA) and sleep bruxism (SB) may appear concomitantly. Data on the relationship between OSA and SB are limited. It was shown that in a population with an increased risk of OSA, OSA was dependently correlated with SB on the degree of OSA severity only in mild and moderate cases of OSA. We aimed to confirm this relationship and affecting factors in a group of dental office patients in a prospective, observational study. Adult patients (n = 119) were evaluated using respiratory polygraphy. The risk of OSA was assessed using a STOP-Bang questionnaire (SBQ). The episodes of bruxism and respiratory events were scored according to the standards of the American Academy of Sleep Medicine. The prevalence of OSA and SB was found to be 63.02% and 41.17%, respectively. The bruxism episode index (BEI) was increased in the group with a higher risk of OSA (SBQ ≥ 3) compared to the group with a lower risk of OSA (3.49 ± 3.63 vs. 2.27 ± 2.50, p = 0.03). The sensitivity and specificity of the SBQ were not sufficient to predict SB. A positive linear correlation between AHI and BEI in the group with AHI < 23/h was found. The study confirmed that OSA was associated with SB in the group of patients with OSA and/or SB risk. The relationship between OSA and SB depended on the degree of severity of OSA and occurred in mild and moderate cases of OSA.