South Shore Schooners

On September 13, 2008, the team showed that Chester could compete at the Junior C level by playing their first ever exhibition game and beat the Liverpool-based South Shore Wild by a score of 4–3.

The Chester Clippers won the 2009–10 Ice Dogs Early Bird Pre-season Tournament with a 6–3 win over the Eastern Shore Jr. Mariners in the final game on September 27, 2009.

Chester then went on to defeat Fundy (quarter-finals), Shannon (semi-finals), and Barrington (finals) to win their second straight Nova Scotia Junior C Hockey League and provincial championship.

[2] The Clippers went 2-2 in the round-robin portion of the 2013 Maritime-Hockey North Junior C Championships and finished 4th out of 5 teams, to advance to the semi-finals, where they suffered a heart-breaking 5–4 loss to the eventual tournament champions, Hampton Hurricanes.

On Monday July 22, 2013, the Nova Scotia Junior "C" Hockey League's Board of Governors approved the transfer and relocation of the defending champion Clippers to a group based in Industrial Cape Breton.