After the failed and short-lived Lakeshore Pirates folded in 1999, the town of Goderich pushed for a new team. They were granted expansion in 2003 after the folding of the Wiarton Wolves. The team was named the Sailors after another Junior C team that had folded in 1993.
In 2004-05, the Sailors squeezed into the fourth and final playoff spot. With an automatic berth to the Western league semi-final, the Sailors met up with the Wingham Ironmen. The Ironmen swept the Sailors 4-games-to-none.
The 2005-06 season ended with the Goderich Sailors in fourth place. In the playoff quarter-final, the Sailors drew the fifth seeded Walkerton Hawks for a best-of-3 series. The Hawks made quick work of the Sailors and won the series 2-games-to-none.
The 2006-07 season saw the Goderich Sailors end the years in last place, the sixth seed. In the Western league quarter-final they again drew the Walkerton Hawks, but this year in the best-of-5 series. The Hawks, who were coming off of a rather strong regular season, defeated the Sailors 3-games-to-1.