Canada. A First and Second War Group to Cpl. Bailey, City of Winnipeg Battalion

A 1914-15 Star, in bronze, full size, reverse impressed 72207 PTE. J. R. BAILEY. 27/CAN:INF:, light wear, very fine. 
A British War Medal, in silver, full size, rim impressed 72207 CPL. J. R. BAILEY. 27-CAN. INF., light contact, very dark patina, very fine. 

A Victory Medal, in bronze gilt, full size, rim impressed 72207 CPL. J. R. BAILEY. 27-CAN. INF., light wear, near very fine. 

A Second War Defence Medal, in silver, full size, light wear, dark patina, very fine. 

A Canadian Volunteer Service Medal, in silver, light wear, dark patina, very fine. 

A Second War British War Medal, in silver, full size, light wear, very fine. 

A 27th Infantry Battalion “City of Winnipeg Regiment” Cap Badge, in browning copper with a clear lacquer overlaid on the obverse, two lugs on the reverse, measures 39 mm (w) x 42 mm (h), 

The St. John Ambulance Association Medal, in bronze, reverse engraved 253133 JOHN R. BAILEY, and impressed REGISTERED AT ST. JOHNS GATE CLERKENWELL, measures 40.2 mm (w) x 43.6 mm (h), light wear, dark patina, very fine. 

An RCAF Reserve Pin, in zinc, measures 23.8 mm (w) x 23.8 mm (h), screwpost on the reverse with small screwplate, light wear, very fine. 

A June 17 1944 Pin, in silvered bronze and enamels, pin on the reverse, marked B.B. Co. [indecipherable], measures 23 mm (w) x 32mm, slight loss of silver finish, very fine. 

A Second War General Service pin, in silvered white metal with red and blue enamels, screwpost on the reverse, numbered 154365, screwplate included, measures 14.9 mm (w) x 22.3 mm (h), light wear and loss of silver finish, remains near very fine. 

A Canadian Base Reinforcement Engineers Overseas Training Wing Tie Pin, in silver and enamels, screwpost on the reverse with screwplate included, measures 10.6 mm (d), marked STERLING on the reverse, light wear, enamels intact, very fine. 

Footnote: John Roland Bailey was born in Sufoldshire, England on July 15, 1892. He was employed as a clerk when he enlisted on May 10, 1915 in Winnipeg. 

In October 1915, Bailey suffered from a gunshot wound to the right arm, and bomb wounds to the right hand. He was later hospitalized due to tonsillitis at the end of January in 1916. He was promoted to acting corporal with pay in August 1916. He was confirmed in the rank of corporal in November 1918.

The 27th Regiment, City of Winnipeg, was a Canadian militia infantry unit that contributed trained soldiers to the Canadian Expeditionary Force during the First World War. While the regiment itself did not deploy overseas as a complete battalion, its members were drafted into various CEF units, including the 8th and 11th Battalions, which saw extensive action on the Western Front. Soldiers from these battalions participated in significant engagements such as the Second Battle of Ypres in 1915, where Canadian troops endured the first large-scale poison gas attacks, the Somme offensive in 1916, marked by intense trench warfare and high casualties, and the Battle of Vimy Ridge in 1917, a defining victory for the Canadian Corps. Through these deployments, men from the 27th Regiment played a key role in Canada’s contributions to major battles in France and Flanders, linking their local militia roots in Winnipeg to the broader national war effort.