Ever since John Wooden retired, playing in the NCAA tournament on a consistent basis has meant, without exception, that you will lose tournament games on a consistent basis. To pile up the appearances is to pile up defeats in March. It is a post-1975 structural given of the sport.
Take Bill Self. This weekend Oregon defeated Kansas in the Midwest regional final, bringing the Jayhawks head coach's career record in the Elite Eight down to 2-7 (including one loss each from his time at Tulsa and at Illinois). For KU fans to be disappointed or even devastated that their top-seeded team didn't make the Final Four is natural and unavoidable.
Still, there are two things to keep in mind when speaking of a coach who's been to the Elite Eight nine times and won just two games.