He started for the varsity football team at Central Dauphin East High School at punter, placekicker, defensive back, quarterback and wide receiver. He was a four-time first team All-Mid Penn Conference punter,[1] and a three-time all-state selection.[2] Webster committed to Purdue on October 4, 2009.[3] Once he committed, he was projected to be the most likely Boilermaker to be a true freshman starter, because starting punter Chris Summers was graduating.[4] He signed his National Letter of Intent with Purdue on February 3, 2010.[5] Upon graduating, he was considered to be the twenty-fifth best placekicker in the national high school class of 2010 by Rivals.com and the thirty-fourth best kicker by ESPN.[6][7]
Webster played college football for the Purdue Boilermakers where he majored in agriculture.[8] During the 2010, 2011, 2012 and 2013 seasons he was the Boilermakers first team punter.[8] When Webster kicked a 79-yard punt for the 2010 Purdue team against Northwestern, it was the longest punt of his career.[9] In 2010, although true freshman Webster placed fifth in the conference in overall punting average (43.3 yards/punt).[10] He earned honorable mention All-Big Ten honors during the 2010 and 2012 seasons, while also earning first-team All-Big Ten honors in 2013 and second-team All-Big Ten honors in 2011.[8] Webster lead the Big Ten in punting average as a senior.[11]