Strong performance by petroleum, engineering, textiles and gems and jewellery sectors propelled the country's exports growth during the month.
India's exports stood at USD 22.1 billion in the corresponding month a year ago.
The total outward shipments had registered a 19.7 per cent growth in April this year.
India's imports too increased by 33 per cent to USD 37.85 billion in May this year.
The previous highest level for trade deficit was in November 2014 when it was recorded at USD 16.86 billion.
Commenting on the figures, exporters body FIEO exuded confidence that the shipments will continue to record positive growth in the coming months.
"The exporters are of the view that the timely support will help in giving further fillip to this growth trend. Challenges with regards to currency appreciation and protectionism should also be looked into by the government," the Federation of Indian Export Organisations (FIEO) President, Ganesh Gupta, said in a statement.
Imports too rose by 40.63 per cent to USD 75.74 billion, leaving a trade deficit of USD 27 billion.
"Exports have been exhibiting positive growth for the last eight months," the commerce ministry said.
During May, major commodity groups of export having a share of 72 per cent in total export basket which have shown positive growth over the corresponding month of last year are engineering (8.25 per cent), gems and jewellery (6 per cent), Petroleum Products (24.92 per cent) and textiles (8 per cent).
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