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HAMILTON, N.Y. -- It was a June day in 2006 when Bobby Pennington visited Colgate to interview for the job of running the school's men's and women's tennis programs.
He arrived in the morning, met with the Colgate athletics administration, toured the campus, and learned more about the tennis teams. One thing he recalls clearly was that administrators were interviewing candidates for two different positions.
Fast forward two decades, and Pennington is one of three Colgate coaches marking their 20-year anniversary, along with volleyball coach Ryan Baker and soccer coach Erik Ronning.
While administrators met with Pennington in one room, they were also interviewing Baker in the room next door.
At the time, Pennington had completed two seasons as head coach of the men's and women's tennis program at D-III Juniata College in Pennsylvania. It was his first time as a head coach. Now, he was looking for a new opportunity, and the prospect of coaching a D-I program at a school such as Colgate intrigued him.
He was offered the Raiders job a week later, and Pennington accepted. He began the role on July 1 -- the same day Baker started his post.
"I was definitely apprehensive and nervous," Pennington, a graduate of Altoona Area High School, said. "To make the jump to a Division I program, I was definitely nervous at the time."
Pennington stepped into a program that had gone through four head coaches in five years. His goal was to bring stability and a winning attitude, much like what he experienced as a tennis player at Kalamazoo College in Michigan, where he was part of a dynasty.
At Colgate, success came quickly for Pennington. It gave the young coach a huge boost in confidence.
"I was fortunate that in my first year, I had two winning seasons," he said. "Both teams were top three in the league. That showed me I could do it."
His longevity at Colgate is something he could not have imagined as a 25-year-old.
"It's definitely very humbling," he said. "You see so much turnover nowadays in college athletics, whether it's Colgate or elsewhere. I give credit to a lot of people, ranging from the players to their parents who have been so supportive of me, and to the Colgate administration. It has been a really long ride, that's for sure."
He credits the Colgate athletics leadership for believing in an inexperienced coach back in 2006.
"I'm really grateful for the opportunity," he said. "Looking back at it now, I see how unique and special it was to get that opportunity at that age. They took a chance on me."
Pennington is approaching 400 victories. He is the longest tenured women's tennis head coach at Colgate, a feat he reached in 2024-25 after 19 seasons. He has coached some of the most successful teams in program history -- like the men's team that finished 15-5 in 2017-18.
Plus, he's experienced special moments on and off the court that have a place in his heart. While victories are special, so are the bonds he's formed and the progress he's seen in his student-athletes over the years.
"There are definitely a number of individual success stories that I'm really proud of," Pennington said. "We've had kids who walked on to the team and became starters. We've had a few Rookies of the Year and a Player of the Year on the men's side. Those are special. We've had great individual achievements, whether it's a player who stuck with it for four years and waited until their fourth year to start or whether it's a kid who played No. 1 for all four years and had an amazing career."
Pennington has also seen eight of his assistant coaches move on to run collegiate tennis programs of their own.
There are a few things that have kept Pennington at Colgate. First and foremost is his family. His three children have grown up in Hamilton and have loved it.
Other reasons are the culture of the tennis program and the relationships he has developed, not just with his student-athletes, but with their families.
He tries to stay in contact with as many of his former players as he can. For special events like Reunion Weekend, he often connects with student-athletes he hadn't seen in years.
Pennington does various things to keep the job exciting. He schedules road matches in other parts of the country against tough programs, a task that requires the head coach to raise funds. Last season, the team played against two opponents in San Diego. The season before that, they traveled to the University of Miami.
The team looks forward to such trips each season, and Pennington does everything he can to make it happen.
"I've learned that the players, they see what they get," Pennington said. "They know I'm genuine, and that I want this to be the best four years of their lives. When they see that, they play really hard for me."