During the fall season of his senior year, Webb placed second at the 2000 Foot Locker Cross Country Championships behind Dathan Ritzenhein.

Webb's record was surpassed fifteen years later by Andrew Hunter from Loudoun Valley High School in Virginia with a time of 3:58.25 set on the same track.

During the fall cross country season, he won several meets, including the Wolverine Interregional and the Big Ten Championships (both 8 kilometer races) in times of 25:12 and 23:19.9, respectively.

Webb competed in this race at the NCAA Outdoor Track and Field Championships a few weeks later, finishing in fourth place with a time of 3:43.23.

Shortly after the completion of the outdoor season, Webb decided to leave the university to turn professional and return to his high school coach and mentor Scott Raczko.

On July 6, 2007, Webb won the IAAF Golden League meet 1500 m race in Paris in a lifetime best of 3:30.54, third fastest on the American list.

After many disappointing results since breaking the American mile record, Webb decided in August 2009 to move to Portland, Oregon to train with coach Alberto Salazar.

[8] In 2010, Webb underwent surgery for an Achilles tendon injury and returned at the Fifth Avenue Mile in September, finishing in fourth behind defending champion Andrew Baddeley.

Alan Webb married Julia Rudd in October 2010, who also enjoys running and is an assistant coach for a high school cross country team.

[14] A convert to Catholicism and LIFE Runners member,[15] Alan and Julia have four daughters, Joanie, Paula, Gabriella (Gabby), and Bridget.