Where did the term 'Ivy League School' originate?

It appears that inspiration for the term "Ivy League" originated with the ivy walls of the oldest colleges.

Students have long revered the ivied walls of older colleges. "Planting the ivy" was a customary class day ceremony at many colleges in the 1800s.

https://en.wikipedia.org/wiki/Ivy_League#History

The term "Ivy" was first used in reference to a group of colleges by sportswriter Stanley Woodward (1895–1965) in 1933:

"A proportion of our eastern ivy colleges are meeting little fellows another Saturday before plunging into the strife and the turmoil."

It appears to have stuck. Shortly after, the first known instance of the term Ivy League being used appeared in The Christian Science Monitor (February 7, 1935).

Several sportswriters and other journalists used the term shortly later to refer to the older colleges, those along the northeastern seaboard of the United States, chiefly the nine institutions with origins dating from the colonial era, together with the United States Military Academy (West Point), the United States Naval Academy, and a few others.

The "IV" myth debunked:

In the "IV myth", the supposed "IV League" was formed over a century ago and consisted of Harvard, Yale, Princeton, and a fourth school that varies depending on who is telling the story. However, it is clear that Harvard, Princeton, Yale and Columbia met on November 23, 1876 at the so-called Massasoit Convention to decide on uniform rules for the emerging game of American football, which rapidly spread.

https://en.wikipedia.org/wiki/Ivy_League#History

[ This is a FunTrivia FAQ, and so this top post has been edited heavily from the original to act as a placeholder for the "best" answer ]

From the Cornell Infobase:

The idea of an Ivy League was derived from James Lynah's policy to form closer bonds with the larger, older universities in the east. Policy called for the 'formation of a League, to reassert amateur principle, to adjure the current athletic sordidness and cynicism, to save, in short, athletic idealism.' (Morris Bishop, History of Cornell)

For years, the Ivy members already had been allied in leagues in basketball, ice hockey, baseball and swimming. Further common competition was found in the Heptagonal Games Association, which included Army and Navy, in the sports of baseball, track and field, and swimming. Through these other scheduling arrangements, the Ivy athletic directors were used to dealing with each other in matters of administration or the exchange of calculated confidences.

As a result of these dealings, and through extensive presidential meetings and discussions, the first 'Ivy Group Agreement' - addressing only football - was signed in 1945. While the 1945 statement did not address any scheduling issues, it did affirm the observance at the eight institutions of common practices in academic standards, eligibility requirements, and the administration of financial aid for athletes. These tenets are what still bind the Ivies together today and all continue to be based on the desire to secure competition with others having like philosophies. The athletic directors, at the direction of the presidents, were then more formally organized as a committee for cooperative endeavor in the details of athletic administration and a dean from each school was appointed to committee to exchange information on eligibility and to act for the presidents in cooperation with the athletic directors.

http://www.not-rocket-science.com/harvardsoccer/historyi.htm

I've always thought that it derives from the popular image of ancient university buildings as covered in ivy (cf Tom Lehrer's 'ivy-covered professors in ivy-covered halls'). This is supported by some reference books and websites.

Another explanation favoured by some people is that a sporting league originally set up by Harvard, Princeton, Columbia and Yale was called the 'Four League' and written with a Roman numeral as 'The IV League': this was read as 'Ivy League'.

Over a century ago, an interscholastic athletic league was formed by Harvard, Yale, Columbia, and Princeton. It was officially known as the 'Four League.' The Roman numeral 'IV' was often used instead of the word four and the term 'IV League' came into use. When spoken, the IV was spelled out and sounded like 'Ivy League.'

http://www.urbandictionary.com/define.php?term=Ivy%20League

The designation 'Ivy League' first appeared at the typewriter of Caswell Adams of the New York Tribune in 1937. The tag, premature of any formal agreement, was immediately adopted by the press as a foreshadowing of an eastern football league which at the time, was big news to everyone except the athletic directors involved.

For years, the Ivy members had already been allied in leagues in basketball, ice hockey, baseball and swimming. Further common competition was found in the Heptagonal Games Association, which included Army and Navy, in the sports of baseball, track and field, and swimming. Through these other scheduling arrangements, the Ivy athletic directors were used to dealing with each other in matters of administration or the exchange of calculated confidences.

As a result of these dealings, and through extensive presidential meetings and discussions, the first 'Ivy Group Agreement'-addressing only football-was signed in 1945.

http://www.not-rocket-science.com/harvardsoccer/historyi.htm

from sportswriter mind:

Many believe, incorrectly, that the name of this group of prestigious East Coast universities derives from an athletic league that originally had four members, the name coming from the Roman numeral IV.

Ivy League is originally a sportswriter's term, but it has nothing to do with the number four. The term was first used in 1937 by the New York Herald-Tribune sportswriter Caswell Adams. He used it in reference to the unofficial conference of teams also known as the Old Ten. The teams were Army, Brown, Columbia, Cornell, Dartmouth, Harvard, Navy, Pennsylvania, Princeton, and Yale. In 1940, Army and Navy dropped out of the association and the membership has remained the same ever since. The league was formalized in 1954 and played its first games as a formal organization in 1956. (Source: 1993 Information Please Sports Almanac)

The term Ivy Colleges is a few years older, first appearing in the Herald-Tribune in 1933 by sportswriter S. Woodward.

The name derives from the ivy that supposedly climbs the walls at these venerable institutions.

As a means to differentiate East coast college athletics from everyone else

http://www.collegeconfidential.com/dean/000054/

http://www.bestcollegereviews.org/history-ivy-league/

https://penncurrent.upenn.edu/2002-10-17/ask-benny/ask-benny-ivy-league-fiction-facts

The last reference, from the University of Pennsylvania (my alma mater) purports to know the true story. I would take it with a grain of salt, however, as there are numerous stories concerning the origin of the term. And yes, there was ivy on the walls of the quad during my stay there...

There was plenty of ivy on the walls when the term was coined in the 30s--these schools have been growing it a while. However, this site will explain my take

answers.yahoo.com/question/index?qid=20080318141155AA0ZEBt no longer exists