Liquidated damages clauses are foundational instruments in modern commercial contracting, enabling sophisticated parties to pre-allocate risk, ensure financial predictability, and reduce post-breach transactional costs. Despite their ubiquity in cross-border agreements, the enforceability of such clauses diverges markedly across jurisdictions, generating significant uncertainty in international arbitration proceedings. This paper undertakes a systematic comparative analysis of the treatment of liquidated damages under English and Indian law, organised around three analytically distinct dimensions: (i) the structural characterisation of liquidated damages provisions; (ii) the allocation and shifting of the evidentiary burden; and (iii) the threshold requirement for proof of actual loss. In English law, the UK Supreme Court's landmark ruling in Cavendish Square Holding BV v Makdessi [2015] UKSC 67 fundamentally reconstituted the classical penalty doctrine by relocating its central inquiry from adequacy of pre-estimated loss to proportionality against the innocent party's legitimate interest in performance. Indian law, by contrast, remains anchored in Section 74 of the Indian Contract Act, 1872, which conditions recovery upon proof of actual loss and caps compensation at a judicially assessed 'reasonable' quantum. Through doctrinal analysis of foundational case law and comparative legal methodology, this paper identifies structural deficiencies in Indian jurisprudence that undermine contractual certainty and generate protracted disputes over damages quantification. Contextualising these findings within international commercial arbitration — supported by empirical data from the ICC, SIAC, and LCIA — the paper demonstrates that Indian law is rarely selected as governing law despite India's considerable presence as a participant jurisdiction. Three targeted legislative and judicial reforms are advanced to modernise India's approach, enhance commercial predictability, and strengthen India's position as a hub for international arbitration.