Gates designed by Chapman & Oxley, sculpture by Charles D. McKechnie. Erected to commemorate the 60th anniversary of Confederation. Structure designated under the Ontario Heritage Act in 1987. It is named the Princes' Gates for Princes Edward (then Prince of Wales, the future King Edward VIII) and George (the future Duke of Kent), who were both in attendance at the ribbon cutting on 30 August 1927.

The pillars on either side of the main arch represent the nine provinces that made up Canada at the time the Gates were completed. The central arch is topped by the statue of the Goddess of Winged Victory, with various smaller figures representing progress, industry, agriculture, arts and science.

The construction of these gates allowed better access from downtown; access to the CNE had previously only been through the Dufferin Gate. The plaza to the east of the Gates was re-landscaped in 2006. The original statue deteriorated heavily over time, and was removed and replaced with a replica in 1987.

A plaque attached to the Gates reads:

The Princes' Gates were officially opened on August thirtieth MDCCCCXXVII by H.R.H. The Prince of Wales accompanied by H.R.H. Prince George. First to pass through these gates was a veterans' parade under the auspices of the Canadian Legion - The British Empire Service League for review by H.R.H. The Prince of Wales.

An Ontario Heritage Trust plaque reads:

This entrance to the Canadian National Exhibition grounds was built in 1927 to commemorate 60 years of Canadian Confederation. The stone and concrete gates were designed by the Toronto firm of Chapman and Oxley and are a fine example of monumental architecture in the Beaux-Arts mode. Sculptor Charles D. McKechnie created the statues. The Winged Victory atop the central arch is flanked by figures representing the CNE's commitment to progress through industry, education and the arts. The gates were opened officially on August 30, 1927 by Edward, Prince of Wales, and Prince George. They have been known ever since as the "Princes' Gates".

One of three plaques erected by Heritage Toronto in 2006 reads:

These monumental gates were erected in 1927 to mark the 60th anniversary of Canadian Confederation. Designed in the Beaux-Arts style by the Toronto firm of Chapman and Oxley, the gates - including the sculptures - were constructed of "artificial stone" made from cement. The sculptures were modelled by Charles D. McKechnie. 

Designed during a period of great national confidence, the gates use the style of ancient Greece and Rome to celebrate both Canada and the Canadian National Exhibition. Originally named "The Diamond Jubilee of Confederation Gates", the structure was renamed the "Princes' Gates" for Edward, Prince of Wales, and his brother Prince George, who were both present at its official opening on August 30, 1927.

• Architect - Chapman & Oxley  <-- More buildings by this architect.
• Architect - Nexus Architects  <-- More buildings by this architect.
• Facade Supplier - Global Precast
• Masonry - Clifford Masonry
• Sculptor - Charles D. McKechnie
• Stone supplier - Peerless Artificial Stone Limited