Ivailo Gabrovski is a Bulgarian former racing cyclist. He holds the record for most Tour of Bulgaria wins, which he won 5 times.

The Tour of Bulgaria is an annual international professional bicycle race held in Bulgaria that was first staged on 21 August 1924. It is part of UCI Europe Tour and is category 2.2. The race covers about 1,500 kilometres and lasts two weeks. As of 2017, 66 editions were held. The longest length of the race was in 1949 – 1905 km. The course changes every year, but the race has always started in Sofia.