Background: Outdoor work is associated with high and chronic exposure to solar ultraviolet radiation which might lead to an increased risk of developing skin (pre)malignancies. Prevalence of actinic keratosis (AK), basal cell carcinoma (BCC), cutaneous squamous cell carcinoma (cSCC) and cutaneous melanoma (cM) in Dutch outdoor workers (OW) has not previously been investigated. Objective: This study compares the prevalence of premalignant lesions and skin tumours in OW and matched controls (non-OW). Methods: In a population-based cohort study, prevalence of premalignant lesions and skin tumours was investigated in a group of OW (n = 841) and controls matched 1:1 by age, sex, skin colour and tendency for sunburn. Skin examinations were conducted by physicians and skin cancer history was derived from the nationwide Dutch Pathology Registry. Information on OW was obtained through interviews. Conditional logistic regression models were used to calculate odds ratios (ORs) with 95% confidence intervals (CIs) for associations between OW and BCC, cSCC, cM and (number of) AK. Results: AK was found in 22.7% of OW and 22.9% of non-OW, BCC in 14% of OW and 15.7% of non-OW, cSCC in 4.9% of OW and 3.4% of non-OW, and cM in 1.9% of OW and 2% of non-OW. There was no significant association between OW and premalignant lesions and skin tumours, with exception for developing ≥4 AKs (OR 1.3 [95% CI 1.0–1.78]). Conclusions: This study reveals high prevalence of premalignant lesions and skin tumours in a Dutch population. No association between OW and the occurrence of premalignant lesions and skin tumours was found, however, multiple AKs were more prevalent in OW.