I assume you're asking if we've ever had such a jump in age from someone younger to someone older?
Because in that case, the answer is no (though we've come close). The record to date would be when Carter passed the torch to Reagan, who was 13 years 8 months older than him. Obama to Clinton is a difference of 13 years 10 months, so that would be a new record, in terms of the age jump from a younger president to an older president.
However, there *have* been larger age jumps going the other way (from old to young), the biggest one being Eisenhower to Kennedy.
I think that the difference in age between Eisenhower and Kennedy was almost 30 years if I'm not mistaken.
On January 20, 1961, Eisenhower was 70 years and 98 days old.
At that time Kennedy was 43 years and 236 years old.
As a result, the age difference between the outgoing and the newly sworn-in president was 26 years and 227 days.