What is the oldest trophy in pro football?

Answer 1

In 1852 Yale and Harvard competed in the first ever intercollegiate sporting event in all of North America. The sport was a rowing race in New Hampshire, on Lake Winnipesaukee. Harvard beat Yale by two lengths. General Franklin Pierce "New Hampshire's favorite son" awarded Harvard the first place prize, a pair of black walnut, silver inscribed trophy oars. To date the trophy oars are the oldest intercollegiate athletic trophy prize in all of North America.

The above was only a one time, singular event and if one considers those oars as really a "trophy".

The oldest college/university trophy continually/annnually contested for in North American sports is the Yates Cup. The Yates Cup is emblematic of the Ontario University Football Championship and was first contested for in 1898. One of four regional/divisional conference football trophies (Ontario (Yates Cup), Quebec (Dunsmore Cup), Canada West (Hardy Cup) and Atlantic (Jewett Trophy/Loney Bowl)) and as a lead up to the two national semi-final bowl games (Uteck and Mitchell Bowls) and then finally to the Vanier Cup, the Canadian Interuniversity Sports (CIS) football championship.

The Yates Cup trophy is second only to the Stanley Cup in age for an annually contested for sports championship.

The question was answered correctly in the beginning top paragraph. It was not a one time event. The 1852 Yale Harvard race being the first College Sports competition in all of North America (also continually to date and annually contested) resulted in a first place prize. Therefore resulted in (to date) the oldest intercollegiate sports trophy in America. The oars were the first place trophy awarded to Harvard. And the event was the first college sports competition ever in America!