Chile pepper (Capsicum annuum) is an increasingly important crop worldwide, and Vietnam and Myanmar are major producing countries. The chile pepper markets in Myanmar and Vietnam are different, with production primarily for domestic consumption in Myanmar and for the export market in Vietnam. However, there is an overall lack of domestically developed cultivars in both countries. The objective of this study was to identify high-performing chile pepper entries, adapted to local conditions, for use in domestic breeding programs or direct release. Fruit length, width, weight, and yield were measured during two seasons (2016–17 and 2018–19), and the same entries were evaluated in Hanoi, Vietnam, and Nay Pyi Taw, Myanmar. However, different entries were tested in each season. During the 2016–17 season, AVPP1324 grown in Hanoi had the overall highest yield (15.3 t·ha–1), followed by AVPP1330 (15.0 t·ha–1 in Hanoi) and AVPP1111 (14.4 and 14.9 t·ha–1 in Hanoi and Nay Pyi Taw, respectively). AVPP0303 had the greatest fruit length, fruit width, and fruit weight in both Hanoi and Nay Pyi Taw during the 2016–17 season. During the 2018–19 season, AVPP1345 (24.8 t·ha–1) followed by AVPP9905 (22.5 t·ha–1) in Nay Pyi Taw, and AVPP1245 (17.4 t·ha–1) in Hanoi had the highest yield. AVPP9905 had the greatest fruit weight and width in both locations. AVPP1345 and AVPP9905 had the greatest fruit length during the 2018–19 season. There is an obvious need for domestically produced cultivars in Myanmar and Vietnam that meet local farmer and consumer preferences and that are adapted to the pests, diseases, and stress in each country. Several high-performing lines were identified that can be used as direct release or incorporated in local breeding programs for the development of inbred or F1 hybrid cultivars. This research also provides a basis for future studies on stability of yield and yield components in Southeast Asia.