The team of 21 players was led by head coach Herman "Billy" Suter and future College Football Hall of Famer and captain Henry "Ditty" Seibels.

With just 18 players, the team known as the "Iron Men" embarked on a ten-day, 2,500 mile train trip, where they played five games in six days.

"[3][4][b] Despite being from a small Episcopal university in the mountains of Tennessee, the Sewanee team came to dominate football in the region during the end of the 19th and early 20th centuries.

[7] Before play started, the Sewanee men trained hard for several weeks under coach Suter.

[8] After a disagreement with traditional rival Vanderbilt University over gate receipts resulting in the 1899 game being canceled, manager Luke Lea sought a way to make up for the lost revenue.

Fullback Ormond Simkins was the star of the 12–0 opening win over the Georgia Bulldogs, netting the first touchdown with a fine line buck of 12 yards through center "amidst thunderous applause".

[26] Sewanee won easily, the first score coming soon after the kickoff on a blocked kick recovered by halfback Quintard Gray.

[27] Sources:[28] In a driving rain at McGee Field, "where each 5-yard line was a miniature stream",[29] Sewanee beat the Tennessee Volunteers 46–0.

[30] The 1899 Iron Men team's most notable accomplishment was a six-day period from November 9 to 14 which is arguably the greatest road trip in college football history.

[31] Contemporary sources called the road trip the most remarkable ever made by an American college team.

Without telling anyone, Lea cleverly arranged for them to be shipped on later trains to arrive in time for the Texas game.

[9][10] The train carrying the players pulled into Austin on the night of the 8th to face the undefeated Texas Longhorns the following afternoon.

[33] Ditty Seibels played throughout the game, scoring both touchdowns, despite his head having split open just above his left eye in the first half and bleeding profusely.

One account reads: "In spite of their long, tiresome trip, the Sewanee men were lively as school boys out for a day off.

[39] Sources:[4] The Tigers arrived in Memphis to play Ole Miss on their third pre-game overnight train ride in five days.

[42] One account reads: "For five minutes after the beginning of the game Cumberland made some good gains, but the Sewanee defense suddenly grew strong, the ball was secured on downs, and Seibels crossed the line for touchdown seven minutes after play began.

"[42] Bart Sims had a school record 11 extra points, and Ormond Simkins rested instead of playing.

Auburn was the only team to score on Sewanee all year, running a fast offense,[46] and played exceptionally well on defense.

[44] Auburn would lock arms to form a wedge for the ball carrier, so Suter told his ends to go at their legs, cleats first.

Sportswriter Fuzzy Woodruff, a witness to the game, wrote:[48][49]Under Heisman's tutelage, Auburn played with a marvelous speed and dash that couldn't be gainsaid and which fairly swept Sewanee off its feet.

They approached this boy...Suter, evidently as mad as fire, asked the down and out player 'Are you fellows going to be run over like this all afternoon?'

[44][49] Sources:[50] The season closed with a 5 to 0 victory over the North Carolina Tar Heels and the championship of the south.

[52][53][f] Included on Suter's All-Southern were: Richard Bolling, Wild Bill Claiborne, Deacon Jones, Rex Kilpatrick, William H. Poole, Ditty Seibels, Ormond Simkins, and Warbler Wilson.

[g] On College Gameday, November 13, 1999, ESPN featured the University of the South with a four-minute segment on the 1899 football team, and CSX Railroad provided a short train ride in Cowan, which was a re-enactment of an early leg of the Sewanee to Texas train ride.

Former Penn State coach Joe Paterno once said: "While there are some who would swear to the contrary, I did not see the 1899 Sewanee football team play in person.

Winning five road games in six days, all by shutout scores, has to be one of the most staggering achievements in the history of the sport.

If the Bowl Championship Series (BCS) had been in effect in 1899, there seems little doubt Sewanee would have played in the title game.

[61] In 2023, David Neil Drews published a book titled Iron Tigers: A novel inspired by the team that conquered Dixie and launched Southern football.