Abe Fortas resigned May 15, 1969 and Harry Blackmun wasn't confirmed until May 12, 1970 (362 days) after the failed nominations of Haynsworth and Carswell. Likewise, Lewis Powell died June 26, 1987 but Anthony Kennedy wasn't confirmed until February 3, 1988 (222 days) after the failed nominations of Robert Bork and Douglas Ginsburg.

There may be other similar situations but those are the ones that came to mind.