However, Fewell has a tricky job of working with two players that do not have a lot of experience at cornerback for different reasons.
Pippens, who was a track star in high school, walked on at Nebraska and eventually earned a scholarship. He appeared in 43 games as a safety for the Cornhuskers, but his only start came when the team opened the game in the nickel defense.
He went undrafted in 2004 and landed with the San Diego Chargers. The night before training camp head coach Marty Schottenheimer told Pippens he would move to cornerback, a position he had virtually no experience playing. He had a chance to play corner in camp and preseason, but it was a slow process.
Pippens started the season on the practice squad where he worked with the scout team. He was elevated to the active roster in Week 7 and spent nearly two months there before being waived in Week 15.
"I was a little surprised when that happened with being on the waiver wire and all that, but everything happens for a reason," Pippens said. "But like anything I do in life, whatever situation I have in front of me, I have to make the best of it and that's what I'm trying to do here."
It took the Bears just one day to sign Pippens. At six-foot-2, 190 pounds they saw something that couldn't be taught, size.
Pippens was again moved to cornerback early in training camp. However, an injury to Jerry Azumah allowed him to get reps as the third cornerback. It has turned into a valuable learning experience for the second year player that had to take in a new position and scheme.
"I've pretty much learned everything pretty fast, so I feel good about my progress, but I have a long way to go," Pippens said. "I look at a lot of these big time corners like Charles Woodson and Bobby Taylor. I (see) them as where I want to get to."
The 25-year-old clinched a victory in the Hall of Fame Game against the Dolphins with a leaping interception in the end zone.
With such triumphs, at times Pippens forgets that he's a novice at the position. On more than one occasion he's overheard what Fewell has said to a veteran and then tried to incorporate the advice to his game.
"It's a daily chore with him because even in walk throughs I kind of say ‘Pippens what are you thinking? Tell me where that came from?' It's a daily process with a guy like him because he doesn't have the experience," Fewell said. "I keep telling him ‘Pip I know you want to try to do things but lets master this craft first before you try new things.' It's quite a battle to try to keep him in check.
"I may tell Charles Tillman something to help put it in his arsenal and Pippens will hear it and he'll want to try it. Then Pip will go ‘but you just said that to Charles.' Yeah, but Charles is a three year veteran, he has experience at corner. Then he'll go ‘oh yeah'."
Pippens' spot on the roster is more secure than that of Davis, who has to impress in two areas in order to make the team.
Davis played receiver in the 2005 Arena League season and caught 100 balls. The Bears believed his skills would be best suited for cornerback, which he hadn't played since 2004.
At first the transition appeared to be overwhelming for the five-foot-9, 180-pound Davis.
"Initially I thought the game might be too big for him because he was frantic a little bit and then he kind of settled down," Fewell said. "So he's settling down each week and trying to get a little bit better each week."
With the return of Azumah imminent, Davis believes his best chance to make the team will be as an offensive weapon.
"We have Nathan Vasher, Peanut and Zoom so I would say more as a punt returner and special teams guy," Davis said of how he believes he can make the team.
Davis has averaged 11.2 yards per punt return. Bobby Wade appears to be the favorite for the role after a 54-yard touchdown against the Colts. Aside from that return he's averaging just 4.8 yards per attempt.
Even though the team is likely to take five corners, Davis knows he needs a strong finish to the preseason.
"(My play) definitely hasn't spoke for itself yet," Davis said. "I still need to go out here like all the other guys that are on the bubble and make some plays. I've got to go out there are really try to pop up on film."
The address pressure from a player can sometimes lead to mistakes in technique.
"Play within the system and you'll be fine," Fewell said. "That's really the big thing I'm going to look for this Thursday. Will they play within the system and use techniques and fundamentals that we've tried to teach them from OTAs up until this point."
Both Pippens and Davis will see extensive action tonight against the Browns and look to make one last lunge toward the finish line.
"Thursday night I'm going out there to try to put together my best preseason football game," Pippens said.
"At this point I'm happy that I've gotten here, but I'm not satisfied that I'm just here," Davis said. "I want to make a statement. I want to go out in this game and make a statement."