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The A&M team had long been planning to play the University of Maryland football team, with Maryland being one of the first two teams the boys had scheduled by late September, the other being their Thanksgiving date against Bingham, a local prep-school. Despite two publications writing the contest would take place on October 25th by October 10th, by the 27th of that month it was announced that "They are trying to arrange a game with the University of Maryland here next Wednesday [November 1st], but have not yet succeeded in doing do." The following day, the game with Maryland was reportedly confirmed to be played that day (The (Raleigh) Morning Post, September 22nd, 1899, p. 5; News and Observer, October 10th, 1899, p. 8; News and Observer, October 27th, 1899, p. 5; The (Raleigh) Morning Post, October 28th, 1899, p. 5).

First, a brief note: this is not the same former-ACC member "University of Maryland" that we know of today--at least, not in the same sense. The present-day University of Maryland is a combination of several formerly-independent Maryland schools and claims the records of the former Maryland Agricultural College. What is contemporarily referred to by some as the "Old" University of Maryland is now the University of Maryland, Baltimore. Maryland Agricultural College later became Maryland State College, and in 1920 became University of Maryland, College Park, its present name that is often shortened to University of Maryland.

Some readers may be wondering: why was the University of Maryland even considering a game against A&M? They weren't exactly a big national draw. Part of the reasoning could be that Old Liners team member Joel Whitaker was a former A&M student, and wanted to meet his former college teammates again. Another park could be convenience--a chance to play a real, if mediocre, college team in the South, which was largely filed with city-organized club or YMCA teams. The A&M game was to come on a planned trip back from Georgia, where the Maryland team had planned to meet the Athens team on October 28th. Georgia reportedly canceled the game due to injuries, but this seems unlikely; on the 28th, Georgia beat Georgia Tech 33-0 in Athens instead of playing a much stronger Maryland team. Instead, the Maryland team began their Southern trip on the afternoon of the 28th, practicing in Henderson for a day before meeting Chapel Hill on the 31st before heading back North. The Farmers and Mechanics were never on Maryland's official schedule (The (Baltimore) Sun, October 28th, 1899, p. 6).

Maryland's football team was not a bad team in 1899, going 3-4-1. To get there, Maryland beat Rock Hill College, of Ellicot City, Maryland, 30-0, Gettysburg College 6-5, and Johns Hopkins 12-0 on Thanksgiving Day. Their 4 losses came mostly to strong teams: North Carolina, 0-6, Georgetown, 0-17, Gallaudet, 0-42, and the Baltimore Medical College, 6-12. Their sole tie was a scoreless match against the Portsmouth Football Association. The team started strong, with 2 of their 3 first wins coming in the start of the season, but followed it up with a 5 game winless streak, reportedly caused by a rash of injuries bad enough that the Maryland team was forced to cancel their long-scheduled game against Carlisle (The Sun Almanac For 1900, p. 37; The (Baltimore) Sun, November 17th, 1899, p. 6).

Though the Maryland team may have planned to play against the Farmers, there was at least one major obstacle to the teams meeting: the Colored Industrial Association Fair. The fair, which ran from 1879 to 1930, opened on the Fair Grounds on October 31st, 1899 (The Times-Visitor, October 25th, 1899, p. 1; Harry McKown). The fair, which met annually in Raleigh to "encourage and promote the development of the industrial and educational resources of the colored people of North Carolina, and to gather statistics respecting their progress in the various pursuits and customs peculiar to civilized and enlightened Nations, to hold annually an exhibition of the progress of the industry and education," was reportedly quite popular in its time. Unfortunately, the Fair took place on the same Fair Grounds that A&M had planned to play Maryland on; this completely annulled any chance of A&M playing just its fourth game against an out-of-state team, no matter how small that chance had been before. Even if Maryland never had planned to play the game, Raleigh papers used the Fair as the reason the game was canceled, though not in a disparaging or racial manner; the Raleigh Times wrote simply "The ball game between the University of Maryland and the A. and M. College, which was scheduled for today, will not take place as the Colored Fair now has possession of the [Fair] Grounds" (The (Raleigh) Times, November 1st, 1899, p. 1).

The Maryland team did, however, play the Tar Heels. The game was widely looked forward to by local football fans, with one paper calling the game the "red letter day" in athletics for UNC. Played in a heavy rain in mud that was reported to be ankle deep, on October 31st, the Tar Heels beat Maryland 6-0 in a game described as "the prettiest game of the season" in Chapel Hill, "so far as real ball-playing was concerned" (News and Observer, October 27th, 1899, p. 3; The Tar Heel, November 8th, 1899, p. 1).