It also can be remembered as one of the best coaching staffs the Big Ten has seen in the last two decades, as two of Ryan's assistants and his director of basketball operations are currently leading programs and have NCAA tournament appearances on their resume.
"That was a heck of staff," said associate head coach Greg Gard, who is the only holdover from that staff and has turned down previous coaching offers. "It was a fun group."
When Wisconsin hosts Virginia Wednesday as part of the annual ACC-Big Ten Challenge, it will mark the first time former assistant Tony Bennett and Ryan have coached against one another since Bennett left following the 2002-03 season to coach with his father, Dick, at Washington State.
In addition to Bennett and Gard, the mix of assistant Rob Jeter (now head coach at Milwaukee) and director of operations Saul Phillips (now head coach at North Dakota State) that made up Ryan's first staff signaled a young eager bunch that had to deal with some adversity right off the start.
Five seniors graduated when Ryan took over before the 2001 season and others decided to transfer. Latrell Fleming collapsed during preseason workouts on the hill and never played after it was discovered he had a heart defect. Andreas Helmigk went down with a knee injury and was lost for the season.
There were times when Wisconsin barely had enough players to run a scout team, meaning Gard would coach out instructions and Jeter and Bennett would work up a sweat against the starters.
"We didn't have to worry about any shot-clock plays because Tony would launch it from halfcourt if he had to," said Gard. "He always liked it when we played zone defense verses man-to-man because he didn't have to run around and guard too many of his kids."
Bennett, 43, is 122-74 in six seasons as a head coach. He coached three years at Washington State after his dad retired and has spent the last three years at Virginia, leading the Cavaliers to a 22-10 record and a No.10 seed in last year's NCAA tournament.
But he'll be best known for his family's contributions to the state. Dick Bennett coached Wisconsin for five-plus seasons, which included 93 wins and leading the school to its second Final Four appearance in 2000. Tony Bennett played for his father at Green Bay before playing three seasons in the NBA, and left the school with his No.25 retired and still ranks as the NCAA's all-time leader in 3-point percentage (49.7).
He also got to see his sister, Kathi, lead the UW-Oshkosh women to a national championship in 1996 and his uncle, Jack, take UW-Stevens Point to back-to-back NCAA Division III titles in the mid-2000s.
"(Tony) does the things the right way," said Gard. "He understands that the simple things make the difference."
The Badgers won a share of the Big Ten Conference title in Ryan's first season, and won the championship outright the next season in addition to advancing to the Sweet 16 of the NCAA tournament.
When Gard started breaking down film of Virginia (4-2), junior guard Joe Harris immediately popped. Second on the team in scoring with an average of 11.3 points a game last season, Harris has elevated his game with the Cavaliers with two key contributors recovering from foot surgery, as he leads Virginia with 15.7 points per game.
Able to score a lot of different ways, Gard was reminded of former UW star Kirk Penney, which should not be a surprise considering Bennett played a significant role in recruiting Penney, along with Devin Harris and Alando Tucker, to Wisconsin during his three-year tenure.
"He can shoot it in transition, they run him off a lot of staggered fade screens, they run some quick hitters for him with some trap doors, things we use to do with Kirk," said Gard. "He reminds me a lot of Kirk with how he can score off the dribble … and they specialize some things for him like we did with Kirk at times."
When asked on Monday, Ryan called Bennett a, ‘guy that knows basketball' and a ‘gym rat,' two reasons why Bennett was the only assistant coach retained by Ryan off of Brad Soderberg's staff.
"You talk about some interesting practices," said Ryan, referring to Bennett's scout team work. "It just showed how tough he was, and he wasn't exactly healthy. I think he got to spend so much time with (trainer) Henry Perez-Guerra that they got to know each other pretty well because Tony was always icing after practice.
"Those guys were definitely under salary that year. Tony was a great leader of the scout team, which shows he was taught by somebody who obviously knows the game."
Ryan was referring to Dick Bennett, but the coaching style of Tony is a hybrid from his father, Ryan and the little nuisances that he's picked up along the way. From things like shrinking the court defensively, making it appear that is more than five defenders out on the court and playing the percentages of not giving open threes, baskets in transitions and looks at the rim, it's a system that has familiar fingerprints all over it.
"He's taken some things he's learned from his dad (and) seen some things that we've done here from an offensive standpoint," said Gard. "You steal from everybody. We've done it, too."
Even so, that hasn't made the scouting report all that easier to do between two old friends.
"I am happy for him," said Gard. "Hopefully he takes one on the chin Wednesday night."