Schobert played college football for the Wisconsin Badgers, winning the Jack Lambert Trophy in 2015, as the nation's best linebacker.

[2] In July 2012, Schobert's outstanding performance in the WFCA Large School All-Star Game in which he played running back, safety and kick returner, tallying 145 all-purpose yards, two tackles, two pass-breakups and an interception caught the attention of Kenosha Bradford football coach Jed Kennedy.

When he learned that Schobert's only opportunity to play Division I college football was as a walk-on at North Dakota, he contacted people he knew in the University of Wisconsin athletic department.

The day before Schobert was to depart for Grand Forks, North Dakota, Badgers head coach Bret Bielema offered him a preferred walk-on spot.

"[4] Schobert attended the University of Wisconsin-Madison, a member of the Big Ten Conference, where he played outside linebacker for the Wisconsin Badgers football team from 2012 through 2015.

Nonetheless Schobert was named as a semifinalist for the Bednarik and Lombardi Awards in addition to the Lott IMPACT Trophy watch list.

[9][10] At the annual Badgers year-end honors banquet Schobert was the recipient of the Jimmy Demetral Team MVP award.

ESPN's Kevin Weidl commented on Schobert being a "savvy" pass rusher and that he "holds up well in space".

Dillon blocked a 33-yard field goal attempt by Ross Martin, Schobert was able to recover the ball and return it for 73 yards to the opposition's 6-yard line before being tackled by Jerell Adams.

[23] Coming out of Wisconsin, Schobert was projected to be a third- or fourth-round pick by the majority of NFL draft experts and scouts.

[29] He competed with Paul Kruger, Barkevious Mingo, Nate Orchard, and Emmanuel Ogbah for the starting outside linebacker job.

The Cleveland Browns released veteran Paul Kruger and traded Barkevious Mingo to the New England Patriots after Schobert showed promise throughout training camp and named the backup right outside linebacker behind Emmanuel Ogbah.

[30][31] He made his professional regular season debut during the Cleveland Browns' season-opening 10–29 loss to the Philadelphia Eagles, finishing with a solo tackle and a pass deflection.

[32] He finished his rookie season with 28 combined tackles (19 solo), a half a sack, and a pass deflection in four starts and 16 games.

[36] In Week 3 against the Jets, Schobert made a game clinching interception to help give the Cleveland Browns their first win since December 24, 2016.

[37] In Week 4 against the Oakland Raiders, Schobert made 14 tackles and sacked quarterback Derek Carr once.

[40] In Week 4 against the Ravens, Schobert recorded a team high 17 tackles and sacked Lamar Jackson once in the 40–25 win.

[41] In Week 9 against the Denver Broncos, Schobert forced a fumble on wide receiver Diontae Spencer that was recovered by teammate Denzel Ward in the 24–19 loss.

[47][48] In Week 6 against the Detroit Lions, Schobert led the team with 10 tackles and recorded his first interception as a Jaguar off a pass thrown by Matthew Stafford during the 34–16 loss.