This study used a stochastic simulation model to estimate the potential economic benefit of using timed artificial insemination (TAI) in combination with conventional unsorted (TCONV) and sexed (TSEX) semen in heifers only (TCONV-H, TSEX-H) and in both heifers and lactating cows (TCONV-HC, TSEX-HC) in a high-producing, pasture-based production system. The scenarios were compared with a conventional reproductive policy (CONV) in which heifers and cows were inseminated with conventional unsorted semen after estrus detection. Sensitivity analysis was also used to estimate the effect of hormone costs from TAI use on the profitability of each program relative to CONV. The mean annual (± standard deviation) profit advantage (ΔPROF) over CONV for TCONV-H, TCONV-HC, TSEX-H, and TSEX-HC scenarios were €3.90/cow ± 4.65, €34.11/cow ± 25.69, €13.96/cow ± 6.83, and €41.52/cow ± 42.86, respectively. Combined application of both technologies was shown to return a greater annual ΔPROF on average compared with that achievable from TAI alone. However, the risk of not returning a positive annual ΔPROF varied across the scenarios with higher risk in TCONV-H and TSEX-HC. Specifically, TCONV-H and TSEX-HC had a 24 and 18% chance, respectively, of not returning a positive annual ΔPROF. Sensitivity analysis showed that when hormone costs increased by €10/cow TCONV-H and TSEX-HC had a 38 and 23% chance, respectively, of not returning a positive annual ΔPROF. The range in ΔPROF for TCONV policies was most sensitive to the TAI pregnancy rate and TSEX policies were most sensitive to the relative fertility achieved with sexed compared with unsorted semen. This study has shown TAI and sexed semen are complementary technologies that can increase genetic gain and profitability in a pasture-based, dairy production system.