Q: How many times has a German Shepherd won Best in Show at the Westminster Kennel Club Dog Show? Good News For Pets 8 years ago A. Two times. A German Shepherd was awarded Best in Show at the 141st Westminster Kennel Club Dog Show at Madison Square Garden in New York, NY for 2017 and in 1987. A German Shepherd named GCH CH Lockenhaus’ Rumor Has It V Kenlyn walked away with this year’s win, besting more than 2,800 dogs representing 200 breeds. The German Shepherd CH Covy-Tucker Hill’s Manhattan, nicknamed “Hatter,” was the winner in 1987. Source: Westminster Kennel Club