The 2 papers have now reported witnesses saw Mr Cummings in Barnard Castle, more than 25 miles from Durham, on 12 April.
On 14 April, he was seen in London. According to a witness, he was found again near Durham in Houghall Woods on 19 April.
Mr Cummings is yet to publicly react to the new claims, however the Sunday Telegraph reports he informed Downing Street he left Durham on 13 April, which the claim he made a second trip from London was “totally false”.
Transport Secretary Grant Shapps told the BBC’s Andrew Marr that the claims of a 2nd journey was “incorrect”.