10 Longest Gaps Ever Between WWE World Title Matches

3. The Big Boss Man - 10 Years, 7 Months, 16 Days

A WWE Hall of Famer, and one of the most iconic performers in the modern history of professional wrestling, The Big Boss Man's career was surprisingly low on World Championship matches. In fact, the big man only had three televised world championship matches in his entire WWE career.

The first of those came in a match that was one of the first pro wrestling bouts that this writer ever saw. On the 21st episode of Saturday Night's Main Event, The Big Boss Man challenged WWF Champion Hulk Hogan for the title inside a steel cage. It was the old fashioned blue cage that generates so much nostalgia in fans from that era, and while Boss Man was unsuccessful in the match, he was clearly positioned as one of Hulkamania's biggest threats.

Over a decade passed before Boss Man got another shot at the World Title, and it was a very different Boss Man by the end of the last millennium. The Boss Man's feud with Big Show isn't exactly remembered for the right reasons, but it was Show who held the title as Boss Man put up a stern challenge - albeit a stern challenge that ended after just three minutes at the final WWF pay-per-view of the 20th century.

The night after Armageddon 1999 saw The Big Boss Man challenge for the WWF Championship for the final time, alongside Albert in a two-on-one handicap match. Big Show retained his championship, confirmed Boss Man's place in the list of greats to have never won the top prize in WWE.