Ashley Westwood, a name familiar to Indian football, has become a recurring obstacle for the nation's aspirations on the pitch. From his trophy-laden stint with Bengaluru FC to his recent successes coaching against the Indian national team, Westwood's tactical acumen and in-depth knowledge of Indian football have consistently proven to be a thorn in India's side.

Most recently, Westwood guided Hong Kong to a crucial 1-0 victory over India in their AFC Asian Cup qualification match in June 2025. This result severely jeopardized India's chances of direct qualification for the 2027 AFC Asian Cup, adding another chapter to Westwood's narrative of challenging India's progress. A late penalty secured the win for Hong Kong, highlighting Westwood's ability to exploit vulnerabilities in the Indian team.

Before his role with Hong Kong, Westwood coached Afghanistan, leading them to a victory over India in March last year. This win not only "rubbed salt in India's wounds," as some reports indicated, but also played a significant role in ending India's chances of direct qualification for the 2027 AFC Asian Cup and ultimately led to the sacking of coach Igor Stimac. Despite missing key players due to a pay dispute, Westwood masterminded a victory against a higher-ranked Indian team, showcasing his tactical prowess and ability to motivate his players.

Westwood's success against India isn't merely coincidental. His three seasons with Bengaluru FC saw him win a major trophy each time, demonstrating his understanding of the Indian football landscape and his ability to build successful teams within it. This intimate knowledge of Indian football, coupled with his tactical flexibility, has allowed him to consistently outmaneuver the Indian national team. In the three games that Westwood has coached national teams against India, he has secured two wins and a draw.

The impact of Westwood's strategies extends beyond mere wins and losses. His victories against India have had tangible consequences, affecting qualification chances and even leading to managerial changes. This underscores the significant role Westwood has played in shaping India's footballing journey in recent years. While India continues to strive for success on the international stage, they will likely need to find a way to overcome the challenges posed by Westwood and his in-depth understanding of the game in India.