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The division was originally formed on 19 March 1923 as the Winnipeg Company, and later renamed The Winnipeg Division in 1936. In 1942, the division was renamed HMCS Chippawa, the name that it retains to the present.
The first Commanding Officer of the division was Eustace Brock, the Assistant Secretary of the Great-West Life Assurance Company. In March 1923 the unit's first quarters were a small office and a classroom located in McGregor Armouries. Later, in the spring of 1924 the division moved into the Rat-Portage Lumber Company building in Norwood, which is still standing today as the Poulin's Exterminators building.
In the years following, the division moved to the old St Matthews Church on the corner of Sherbrook Street and Ellice Avenue, to a condemned fire hall on Gertrude Avenue just off Osborne Street (now demolished), to space at the Security Storage building on Ellice Avenue, and then in October 1942 to the old Winnipeg Winter Club located at 51 Smith Street.
In November, 1941, the unit was commissioned as HMCS Chippawa. Chippawa is named after the vessel which led the line of Commander Robert Heriot Barclay into action against the Americans at the Battle of Lake Erie on 10 September 1813. The ship had been built by the Americans at Maumee in 1810, was captured by the British shortly after the war began, and renamed HM Schooner Chippawa. The schooner was 35-tonne and had a crew of fifteen. She was commanded by Frederic Rolette, a Provincial Marine Lieutenant. Her armament varied from two 8-inch howitzers to her final configuration on the day of battle of one 9-pounder mounted on a swivel. Chippawa was captured by the Americans during the battle, and was later destroyed at the capture of Buffalo, 30 December 1813. The ship itself derived its name from the Indian tribe which inhabited the area near the Saulte at the west end of Lake Superior.
HMCS Chippawa made its greatest contribution during the Second World War. Chippawa recruited a total of 297 officers and 7,567 men, as well as the second-largest contingent of WRENS (Women's Royal Naval Service) in the country, HMCS Chippawa became the third greatest source of naval personnel in Canada, despite being the farthest inland.
CHIPPAWA's tradition of service to community and country continued in the fifties. In the spring of 1950 the Red and Assiniboine Rivers overflowed their banks and threatened the very existence of Winnipeg. Thousands of citizens had to be evacuated from their homes and sent to neighbouring towns and provinces. CHIPPAWA became the centre of flood-fighting activities and naval personnel, both Regular and Reserve, were sent to Winnipeg from all over the country and lived on board CHIPPAWA for several weeks. The Ship's galley was activated and within 48 hours was serving 1,500 meals a day to the flood fighters. CHIPPAWA's Main Drill Deck served as a marshaling area for motor boats and other marine craft used during the flood.
In the early 50s a polio epidemic hit the city and CHIPPAWA's facilities were once again pressed into service. CHIPPAWA's heated swimming pool was used for therapy for polio victims for close to two years following the epidemic.
During the sixties CHIPPAWA participated with pride in Canada's Centennial by building an authentic York boat on the drill deck of CHIPPAWA, and later launched and named her CHIPPAWA II. In 1968, CHIPPAWA provided facilities and support for the Pan-American Games hosted by Winnipeg. It was during this decade that HMCS CHIPPAWA grew to be the largest of all the 21 Naval Reserve divisions with more than 300 members of Ship's Company, comprising all ranks.
In more recent times CHIPPAWA's challenges have been many. A reorganization of Military bands has left the CHIPPAWA band as one of the few remaining official Naval Reserve bands in Canada. Lately, the manning of the Maritime Coastal Defence Vessels has caused many of CHIPPAWA's trained personnel to leave Winnipeg to commission and man the new ships. This has caused challenges to the recruiting system, to replace these people as fast as they depart.
And of course, in the spring of 1997, Manitoba endured another disastrous flood. CHIPPAWA became the home for nearly 200 Naval Reservists from units across Canada. Again, CHIPPAWA's galley put out thousands of meals for the flood fighters, her classrooms became accommodations, and her main deck became a parking lot and repair area for boats of all shapes and sizes. The reserve sailors were tasked to flooded areas all across southern Manitoba. Their finest performance was in the flooded areas just south of Winnipeg where they were instrumental in saving many homes in the area of Grande Pointe and South St. Mary's Road. At the end of the emergency the Commander of Maritime Operations Group Four, Captain Forcier, told all reserves in CHIPPAWA that in the areas just south of Winnipeg "he had witnessed the finest example of seamanship he had ever seen, Regular Force or Reserve." 
In summer of 1998, the old Winnipeg Winter Club building was demolished and a new building was built on the same site. While the building was being built the division paraded in Hangar 11 at 17 Wing Winnipeg. In November 1999, the new naval training building was completed and the division moved back to its downtown Winnipeg headquarters.
Notable former members of HMCS CHIPPAWA: