In 1901, Gregory enrolled in law school at the University of Michigan, receiving his law degree in 1904.
 While attending law school, he played college football as the starting center for Yost"s "Point-a-Minute" football teams.
 During Gregory's three years as the starting center, the team compiled a record of 33-0-1, outscored opponents 1,759 to 18, and has been recognized as a national championship team all three years.
 Gregory started 32 games at center for Michigan as follows:
Gregory started all 11 games for the 1901 Michigan Wolverines football team that finished the season undefeated with an 11–0 record, outscored their opponents by a combined total of 550 to 0 and defeated Stanford, 49–0, in the 1902 Rose Bowl, the first college football bowl game ever played.
The team has been recognized as national champions by the Helms Athletic Foundation, the Houlgate System, and the National Championship Foundation.

Gregory also started all 11 games for the 1902 Michigan Wolverines football team that finished the season undefeated with an 11–0 record, outscored opponents by a combined 644 to 12, and became known as the second of Yost's famed "Point-a-Minute" teams.
 The 1902 team has  been recognized as national champions by the Billingsley Report, Helms Athletic Foundation, Houlgate System, National Championship Foundation and Parke H. Davis.
 Gregory was the only player to start all 22 games for Michigan's 1901 and 1902 national championship teams.

Gregory started 10 of the 12 games played by the 1903 Michigan Wolverines football team that compiled a record of 11–0–1 and outscored its opponents 565–6.
 The 1903 team has been recognized as national champions by the National Championship Foundation.


During a 128–0 victory over Buffalo in 1901, Gregory reportedly asked for an opportunity to run the ball for a touchdown.
 In his history of the Michigan football program, Jim Cnockaert described the incident as follows:
"Dad Gregory, the team's center, complained at one point that everyone on the team had scored a touchdown in the game except him.
 Later, as the Wolverines closed in again on the goal line, [Boss] Weeks signaled for Gregory to line up in the backfield and promised to hand him the ball.
 Gregory plowed through the line and dove into the end zone, yelling, 'I'm over!
 I'm over!'
 However, Weeks played a trick on the play, pulling the ball away at the last second so that Gregory was not awarded the touchdown."


A profile of Gregory in the 1903 University of Michigan yearbook noted:
"While not an exceptionally heavy man, his build attracted early in the fall of 1901 ... Yost tried him at center and he developed rapidly.
 His weight is low down, giving him stability for that position. ...
 In nearly all the games of the past two seasons he has played against men who have outweighed him, but he has never failed to hold his own.
 He is aggressive from the start of the game to the call of time, but his aggressiveness never occasions any undue roughness. ...
He is hard and muscular and his build is well adapted to any kind of heavy athletic work.
 Perhaps the greatest thing about Gregory is his accuracy in passing the ball.
 He keeps his head well and never allows anxiety or excitement to cause a bad pass.
 Whether it is the short pass to the quarterback or the long one to the fullback he is absolutely sure. ...
Gregory and Ellsworth of Chicago divided honors for the All-Western eleven this year, but there is a disposition among Michigan students, however, to consider Gregory as the superior of any Western center."

Prior to the start of the 1903 season, press reports indicated that Gregory and halfback Willie Heston, both of whom had come to Michigan from California with Coach Yost in 1901, might not return to the team.
 The Detroit Free Press reported in early September 1903 that there was "a business chance beckoning rather strongly to both" and that the players were rumored to be in Detroit to meet with Coach Yost.
 In 1903, Gregory was identified as the distributor of "Hurry Up Yost Cigars" in advertising published
In 1901, Gregory enrolled in law school at the University of Michigan, receiving his law degree in 1904.  While attending law school, he played college football as the starting center for Yost"s "Point-a-Minute" football teams.  During Gregory's three years as the starting center, the team compiled a record of 33-0-1, outscored opponents 1,759 to 18, and has been recognized as a national championship team all three years.  Gregory started 32 games at center for Michigan as follows:
Gregory started all 11 games for the 1901 Michigan Wolverines football team that finished the season undefeated with an 11–0 record, outscored their opponents by a combined total of 550 to 0 and defeated Stanford, 49–0, in the 1902 Rose Bowl, the first college football bowl game ever played. The team has been recognized as national champions by the Helms Athletic Foundation, the Houlgate System, and the National Championship Foundation.
Gregory also started all 11 games for the 1902 Michigan Wolverines football team that finished the season undefeated with an 11–0 record, outscored opponents by a combined 644 to 12, and became known as the second of Yost's famed "Point-a-Minute" teams.  The 1902 team has  been recognized as national champions by the Billingsley Report, Helms Athletic Foundation, Houlgate System, National Championship Foundation and Parke H. Davis.  Gregory was the only player to start all 22 games for Michigan's 1901 and 1902 national championship teams.
Gregory started 10 of the 12 games played by the 1903 Michigan Wolverines football team that compiled a record of 11–0–1 and outscored its opponents 565–6.  The 1903 team has been recognized as national champions by the National Championship Foundation.

During a 128–0 victory over Buffalo in 1901, Gregory reportedly asked for an opportunity to run the ball for a touchdown.  In his history of the Michigan football program, Jim Cnockaert described the incident as follows:
"Dad Gregory, the team's center, complained at one point that everyone on the team had scored a touchdown in the game except him.  Later, as the Wolverines closed in again on the goal line, [Boss] Weeks signaled for Gregory to line up in the backfield and promised to hand him the ball.  Gregory plowed through the line and dove into the end zone, yelling, 'I'm over!  I'm over!'  However, Weeks played a trick on the play, pulling the ball away at the last second so that Gregory was not awarded the touchdown."

A profile of Gregory in the 1903 University of Michigan yearbook noted:
"While not an exceptionally heavy man, his build attracted early in the fall of 1901 ... Yost tried him at center and he developed rapidly.  His weight is low down, giving him stability for that position. ...  In nearly all the games of the past two seasons he has played against men who have outweighed him, but he has never failed to hold his own.  He is aggressive from the start of the game to the call of time, but his aggressiveness never occasions any undue roughness. ... He is hard and muscular and his build is well adapted to any kind of heavy athletic work.  Perhaps the greatest thing about Gregory is his accuracy in passing the ball.  He keeps his head well and never allows anxiety or excitement to cause a bad pass.  Whether it is the short pass to the quarterback or the long one to the fullback he is absolutely sure. ... Gregory and Ellsworth of Chicago divided honors for the All-Western eleven this year, but there is a disposition among Michigan students, however, to consider Gregory as the superior of any Western center."
Prior to the start of the 1903 season, press reports indicated that Gregory and halfback Willie Heston, both of whom had come to Michigan from California with Coach Yost in 1901, might not return to the team.  The Detroit Free Press reported in early September 1903 that there was "a business chance beckoning rather strongly to both" and that the players were rumored to be in Detroit to meet with Coach Yost.  In 1903, Gregory was identified as the distributor of "Hurry Up Yost Cigars" in advertising published
George W. Gregory