The rupee fell below the 60-level against the American currency after a gap of over one month by dropping 28 paise to 60.05 on sustained dollar demand from importers amid rise in crude oil prices.
The local currency moved in a range of 59.80 and 60.05 per dollar during the morning trade on Monday.
It had last traded at 60.05 on May 12, 2014.
Crude oil prices rose to nine-month high in Asian trade on Monday as investors kept a wary eye on the worsening crisis in Iraq.
US benchmark West Texas Intermediate for July delivery jumped 35 cents to USD 107.26 a barrel in late morning trade.