Purpose This study aimed to evaluate the medium-term fit of soft contact lenses (SCLs) and its effects on dry eye by using ultra-high-resolution optical coherence tomography (UHR-OCT) and digital slit-lamp biomicroscopy (DSLB) and identify factors indicating a better contact lens fit. Methods A total of 14 participants (7 men, 7 women; mean age, 23.1 years) were recruited. Temporal lag and conjunctival coverage were imaged by UHR-OCT. DSLB was used to assess lens decentration and blink-induced movement. In addition, dry eye indices, including ocular surface disease index (OSDI), tear break-up time (TBUT), and Schirmer I test scores, were measured at baseline and 1 day, 1 week, 1 month, 3 months, and 6 months after wearing. Results Good repeatability was found in the assessments of lens fit characteristics by two researchers and in the assessments by one researcher at different follow-up times. There were no significant differences in lens fit characteristics, TBUT and Schirmer I test scores at each checkpoint (P >0.05). However, the OSDI was significantly higher than baseline after wearing (P <0.05). Changes in the temporal lag were positively correlated with changes in TBUT (r =0.544, P =0.044) and negatively correlated with changes in OSDI (r = -0.629, P =0.016). Changes in blink-induced movement were positively correlated with changes in OSDI, Schirmer I test scores, and TBUT (P <0.05). Conclusions UHR-OCT and DSLB can be used to comprehensively and quantitatively evaluate SCL fit. Both the contact lenses and ocular surface conditions are almost stable within 6 months of SCL wear. Temporal lag and blink-induced movement have a strong correlation with dry eye parameters in SCL wearers.