Odisha, a coastal state in eastern India, has played a vital role in shaping the trajectory of Indian astronomy through its indigenous scholars and traditional knowledge systems. This paper explores the contributions of two key figures from Odisha: Ācārya Śatānanda of the 11th century and Mahāmahopādhyāya Sāmanta Candraśekhara Siṁha of the 19th century. Śatānanda's Bhāsvatī, composed in 1099 CE, introduced innovative centesimal calculations that simplified astronomical computations and foreshadowed modern decimal methods, using multiples of 100 for planetary positions without relying on trigonometry. Sāmanta Candraśekhara, known locally as Paṭhāṇī Sāmanta, authored the Siddhānta-darpaṇa in the late 19th century, refining classical texts like the Sūryasiddhānta through naked-eye observations and crafting precise instruments such as the Svayambhū-yantra and Chapa Yantra. These works reflect the Odishan Knowledge System, rooted in palm-leaf manuscripts, royal patronage, and integration with daily life, including agriculture and rituals. Drawing from historical treatises and commentaries, this study highlights how Odisha's astronomers bridged ancient Vedic traditions with practical innovations, enriching India's astronomical heritage. Their legacies underscore the enduring value of regional knowledge in fostering scientific inquiry.