Carnarvon is a key horticultural district in Western Australia which is located approximately 900 km north of Perth and is characterised by a semi-arid climate. In Carnarvon, capsicum (Capsicum annuum L.) is the second most important vegetable crop after tomato, with approximately 3700 tonnes of capsicum fruit produced annually with a farm gate value of AUD 13.5 million. High temperatures, excessive sunlight, low air humidity, and strong wind in spring and summer are major impediments to the achievement of high yield and quality of capsicum in this region. Capsicums are usually planted between March (early autumn) and May (late autumn), and the harvest is usually finished by October (spring) of the same year when grown under shade net houses. However, the internal microenvironment in the shade net houses is sub-optimal for the crop in the early and late growing season due to excessive temperatures and low humidity, resulting in a shorter harvest window and lower production. This study was conducted to examine the possibilities to extend the cropping season for capsicum varieties (i.e., Chevello and Chevi) grown under the retractable roof production system (RRPS) and explore an alternative protected cropping structure that is more affordable and suitable to grow vegetable crops under Carnarvon weather conditions. Overall, the results showed that capsicums planted in February (planting 1) performed better than specimens planted later on in the season: planting 1 performed better and yielded the highest marketable fruit yield (102.6 t ha−1) compared to those planted in early April (planting 2, 72.5 t ha−1) and late May (planting 3, 36.1 t ha−1). The RRPS effectively mitigated the adverse weather conditions and provided a more optimised internal microenvironment for vigorous crop establishment in late summer and an extended harvest in late spring, leading to a higher marketable fruit yield per crop. The total soluble solids were cultivar-specific, with the Brix level of Chevello changing with planting time while those of Chevi remained constant. The study identifies the potential for an alternative protected cropping structure, i.e., the modified multi-span polytunnels. The technical feasibility and affordability of the alternative protected cropping structure is also discussed.