A cross-sectional study on men who have sex with men (MSM) for the HIV prevention project was conducted to assess the prevalence of HIV infection–related behaviors among 551 MSM recruited in 2008–2009 and 1910 MSM in 2014–2018 for voluntary counseling and testing at a HIV clinic in Chiang Mai. Overall, the study found that the prevalence of HIV infection was significantly decreased from 12.9% (71/551) in the earlier study (2008–2009) to 8.2% (157/1910) in the recent study (2014–2018) ( p = 0.001). By comparison, in 2008–2009 and 2014–2018, there was no statistically significant difference in consistent condom use (39.0% [186/477] vs. 38.9% [591/1512], p = 0.969), while unprotected anal sex with casual partners significantly increased (44.5% [159/357] vs. 51.9% [645/1242], p = 0.014) and receptive anal sex significantly increased (37.7% [180/477] vs. 45.1% [860/1905], p = 0.004). However, previous HIV testing within 1 year increased significantly from 64.6% (197/305) to 74.7% (677/906, p = 0.001). In exploratory multivariate analysis, the factors associated with HIV infection included gay men, age below 20 years, being self-employed, being an employee, having only receptive anal sex, having both receptive/insertive anal sex, being a former substance user, using online dating, having a history of sexually transmitted infection symptoms, self-perception as being at high risk for HIV, last HIV testing >1 year, and never previously testing for HIV. The data represent the trend of health-seeking behavior improvements. The findings demonstrated the need for a novel sexual health service in an endemic setting and health promotion for online partner-seeking.