Crossbreeding is regarded as a faster way than using pure dairy breeds to improve the reproductive performance of dairy cows, which is pivotal to farm income. The reproductive performances of Jersey and Fleckvieh × Jersey (F × J) heifers and cows were compared in a pasture-based production system. Heifers were inseminated when showing signs of heat from 13 months old and cows from 40 days post calving. Using insemination records and pregnancy check results, fertility traits were derived and compared between breeds, using analysis of variance for continuous records. Age at first insemination and conception age for heifers did not differ between the two breeds, resulting in a similar age at first calving. For cows, the mean (± SE) interval from calving to first insemination was shorter for F × J cows, being 76.7 ± 2.2 days compared with 82.4 ± 2.5 days for Jersey cows. A larger proportion of F × J cows were inseminated within 80 days post calving, compared with the Jersey cows (0.70 and 0.54, respectively). Furthermore, the proportion of cows confirmed pregnant by 100 days in milk was higher for F × J cows in comparison with Jersey cows, being 0.79 and 0.66, respectively. Although the absolute number of days between calving and conception (days open) was slightly less for F × J cows in comparison with Jersey cows (104.8 ± 6.8 and 114.8 ± 8.1 days, respectively), the difference was not significant. These results indicate the potential of improving reproductive performance of Jersey cows through crossbreeding with the dual-purpose Fleckvieh.