Abstract Introduction Associations between sleep and cognition are well studied in aging populations. However, less is known regarding the moderating impact of chronotype (morningness vs. eveningness) and sex on these relationships. We aimed to determine the sex-specific moderating impact of subjective chronotype on the association between subjective sleep and subjective cognition in middle-aged and older adults. Methods Participants (N=260, 142 men/118 women) aged 50+ completed surveys measuring subjective sleep [Pittsburgh Sleep Quality Scale (PSQI)], chronotype [Morning-Evening Questionnaire (MEQ)], and everyday subjective cognition [Cognitive Failures Questionnaire (CFQ)]. Moderated regressions determined independent and interactive roles of subjective sleep (PSQI-total, sleep disturbances, sleep efficiency), chronotype (MEQ total), and sex on everyday subjective cognition (CFQ scores: total, memory, distractibility, and blunders). Analyses controlled for age, education, depressive/anxiety symptoms, and sleep medication use. Results Sex moderated the interactive associations of chronotype and PSQI-total on CFQ-total (p=.005) and CFQ-memory (p<.001). Specifically, higher PSQI-total was associated with higher CFQ-total (B=0.87, SE=0.38, p=.02) and CFQ-memory scores (B=0.33, SE=0.13, p=.009) in men with a tendency for eveningness. Sex also moderated the interactive associations of chronotype and PSQI-sleep disturbances on CFQ-memory (p=.04) and CFQ-blunders (p=.02). In men with a tendency for eveningness, greater PSQI-sleep disturbances were associated with worse CFQ-memory (B=2.65, SE=.84, p=.002) and CFQ-blunders scores (B=1.85, SE=0.83, p=.03). In women with a tendency for morningness, greater PSQI-sleep disturbances were associated with worse CFQ-memory (B=2.65, SE=.81, p= .001) and CFQ-blunders scores (B=2.37, SE=0.81, p=.004). Conclusion There are sex-specific patterns regarding the moderating impact of chronotype on associations between sleep and everyday cognition in middle aged and older adults. In men prone to eveningness, worse overall sleep quality and sleep disturbances may exacerbate negative perceptions of overall and memory specific cognitive function. However, in women prone to morningness, greater sleep disturbances may exacerbate negative perceptions of memory and task execution. Further investigating chronotype on objective sleep and cognition in prospective studies may help further explain underlying mechanisms of the impact of sleep on cognition, in addition to sex-specific sleep interventions to mitigate cognitive decline in aging populations. Support (If Any)