The present study was performed to determine the farrowing performance of sows, newborn piglet characteristics, colostrum yield, milk yield and piglet preweaning mortality in a free-farrowing pen compared to a conventional farrowing crate system in a tropical environment. A total of 92 sows and 1344 piglets were included in the study. The sows were allocated by parity into two farrowing systems, either a free-farrowing pen (n = 54 sows and 805 piglets) or a crate (n = 38 sows and 539 piglets). Backfat thickness and loin muscle depth of sows at 109.0 ± 3.0 days of gestation were measured. Reproductive performance data including total number of piglets born (TB), number of piglets born alive (BA), percentage of stillborn piglets (SB) and percentage of mummified foetuses (MF) per litter, farrowing duration, piglet expulsion interval, time from onset of farrowing to the last placental expulsion, piglet preweaning mortality rate, percentage of piglets crushed by sows and number of piglets at weaning were analysed. In addition, piglet colostrum intake, colostrum yield, Brix index and milk yield of sows were evaluated. On average, TB, BA, farrowing duration, colostrum yield and milk yield during 3 to 10 and 10 to 17 days of lactation were 14.7 ± 2.8, 12.8 ± 3.1, 213.2 ± 142.2 min, 5.3 ± 1.4 kg, 8.6 ± 1.5 kg, and 10.4 ± 2.2 kg, respectively. Sows kept in the free-farrowing pen tended to produce more colostrum than crated sows (5.5 ± 0.2 vs. 4.9 ± 0.2 kg, p = 0.080). Piglets born in the free-farrowing pen had a higher colostrum intake than those in the crate system (437.0 ± 6.9 and 411.7 ± 8.3 g, p = 0.019). However, the piglet preweaning mortality rate (26.8 ± 2.9 vs. 17.0 ± 3.8, p = 0.045) and the proportion of piglets crushed by sows (13.1 ± 2.1 vs. 5.8 ± 2.7, p = 0.037) in the free-farrowing pen were higher than those in the crate system. Interestingly, in the free-farrowing pen, piglet preweaning mortality rate in sows with high backfat thickness was higher than that in sows with moderate (37.8 ± 5.1% vs. 21.6 ± 3.6%, p = 0.011) and low (21.0 ± 6.2%, p = 0.038) backfat thickness. Moreover, the incidence of crushing in sows with high backfat thickness was higher in the free-farrowing pen than in the crate system (17.6 ± 3.6 vs. 4.0 ± 5.7, p = 0.049), but this difference was not detected for sows with moderate and low backfat thickness (p > 0.05). Milk yield of sows during 3 to 10 days (8.6 ± 0.2 vs. 8.6 ± 2.3, p > 0.05) and 10 to 17 days (10.2 ± 0.3 vs. 10.4 ± 0.4, p > 0.05) did not differ between the two farrowing systems. In conclusion, piglets born in the free-farrowing pen had a higher colostrum intake than those in the crate system. However, the piglet preweaning mortality rate and the proportion of piglets crushed by sows in the free-farrowing pen were higher than in the crate system. Interestingly, a high proportion of piglet preweaning mortality in the free-farrowing system was detected only in sows with high backfat thickness before farrowing but not in those with low and moderate backfat thickness. Therefore, additional management in sows with high backfat thickness (>24 mm) before farrowing should be considered to avoid the crushing of piglets by sows.