This time, however, he is the incumbent leader, instead of chasing the pack.
After throwing for 1,389 yards, six touchdowns and five interceptions in 11 games last season, Sherer has spent the subsequent spring and summer working on every aspect of his game – from throwing to mobility, from decision making to risk taking.
Even so, Sherer, who is entering his third true battle for the starting quarterback job, knows that consistency is what is going to win him the starting nod.
"I've been through it three times so it's something I'm really used to," Sherer said. "I just got to go out there and do my own thing. It's mine to lose. That's the mentality I have to have. I have to go out there and be a senior, be a leader and show the staff that I can be consistent in my play."
If the Indiana-native had been more consistent, UW likely would not be going through another fall of not knowing who the starter will be come September 5th's home opener against Northern Illinois.
Last fall, Sherer's struggles with the offense, inconsistencies throwing the football and pressing too hard to earn the job made then-senior Allan Evridge win the starting job by default. It was something Sherer publically admitted to and something his coordinator hopes he has learned from.
"It's not a good thing to say," Chryst said of Sherer's admission he didn't play his best in camp a year ago. "It's a good thing to admit it and learn from it. I think that's part of camp. You can identify who's going (to perform). There's got to be a mission to it. That's why we were in the situation we were in last year. The thing you're hoping for, when there's competition, someone wins the job. That's a lot different than having to name someone.
"If you are pressing in camp, I don't know how you are going to do when the bullets are live, so to speak. You want to create an atmosphere when there is pressure, there is expectations and see how they respond to it."
After Evridge performed so poorly that the coaching staff warranted a change, Sherer started the last seven games with mixed results. After a rocky first game against Iowa, Sherer led UW to wins in four of the next five games, but struggled, just like the rest of his teammates, against Florida State in the Champs Sports Bowl, completing just 9-of-16 passes for 132 yards and lost two fumbles in a 42-13 loss.
Nitpick a little further and, excluding the nail-biting victory over Football Championship Subdivision opponent Cal Poly in the regular season finale, Sherer beat three teams that finished the 2008 season a combined 15-22.
Since the end of last season, Sherer has gone to extraordinary lengths to put himself in a better position this time around. Spending time at a elite quarterback camp in Florida last spring, Sherer has attempted to fine tune his mechanics, shorten his throwing motion and throw with less of a whip when he delivers a pass. The difference for Sherer is subtle, but a change for the better.
"I think that my release is quicker (and) I am throwing the ball better," Sherer said. "I didn't start off that well, but it's something that you have to build on. It's something you have to concentrate on and something you have to do in a game, not just practice."
Whoever gets the start at quarterback is going to be blessed with an experienced receiving corps. With the tight ends plagued with injuries throughout the entire season and UW's receiving showcasing nothing but youth and experience last year, the Badgers are loaded with talent. In addition to senior Garrett Graham and junior Lance Kendricks holding down the tight end position, the wide receivers return every major contributor from a season ago, strides that have impressed Sherer.
"They've made huge strides," Sherer said. "I think the reason people didn't know as much about them is because we throw the ball to Travis Beckum so much and Garrett Graham. They're all really good and they all bring their own special thing to the offense. I think that's going to be a real explosive group and when you throw to the tight ends and the running backs that we have, it can be an offense that can put up a lot of points."
With redshirt freshman Curt Phillips having impressed coaches with his ability to make plays with his legs and his arm, Sherer doesn't have to look far in the review mirror to find his competition. If he can utilize his game experience from last season into results on the practice field, Sherer will finally see himself emerge from a fall quarterback competition at the top.
"Obviously having seven games under you belt is something that you can't really teach," Sherer said. "I'm confident about it because I've been in a game situation and played with guys. That's huge. I think that improves your timing and just gives you more confidence. I just need to show that I have the confidence to get it done."