His players have been named all-league 23 times and have earned seven Player of the Month awards. He has coached a Patriot League Player-of-the-Year and two Rookie-of-the-Year honorees, including 2014-15 recipient Jacob Daugherty. Pennington also serves on the ITA Division I Men's Northeast Rankings Committee.
The Raider men enjoyed an outstanding 2014-15 campaign, compiling a 14-7 overall record, highlighted by a 7-1 mark at home, to post the most dual match victories since the 1997-98 season. Colgate rattled off eight straight victories during the regular season, its longest undefeated stretch since an 11-match streak within the 1996-97 season. Picked to finish sixth in the Patriot League preseason poll, the Raiders claimed fourth in the final league rankings thanks to win over League rivals Bucknell, Holy Cross Loyola (Md.), and Lafayette. Daugherty became the program’s third Rookie-of-the-Year honoree while also taking home Second-Team All-Patriot League accolades.
Boasting one of the youngest rosters in the Patriot League, the women also flourished in 2014-15, compiling wins against League foes Lafayette and Holy Cross, as well as Empire State foes Manhattan, Siena, Cortland and Rochester.
Pennington helped turn the men's team from a 6-12 record in 2005-06 to an 11-10 record in 2006-07. The men finished third in the Patriot League with a 4-2 mark, and rode a six-match win streak into the Patriot League Tournament. The Raiders blanked No. 4 seed Lafayette 4-0 in the first round of the Patriot League Tournament, to mark the first win in the league tournament since 2002. Colgate recorded a program first, when three players were named to the all-league teams. In 2007-08 the men's team posted an 8-11 record and finished third in the Patriot League with a 4-3 mark. Martin MacIntyre captured Player of the Year honors along with a place on the all-league first team.
The 2008-09 season eclipsed previous years with the men posting an overall record of 12-8 and finishing second in the Patriot League after regular season play. During the 08-09 season the Raiders won five matches by a score of 4-3, defeated Army for the first time in seven years and advanced to the semi-final round of the conference tournament. Both MacIntyre and John Nogueras were named to the All-Patriot League teams, with MacIntyre earning first team accolades and Nogueras earning second team.
The women's team went from a 9-9 record in 2005-06 to an 11-8 record in 2006-07. Despite being a young squad, the Raiders posted a 3-1 league mark to finish second the Patriot League. Three players were named to the all-Patriot League teams. In 2007-08 the women got off to its best start since 1993-94, winning its first six matches that included three shutouts. With a 2-2 mark in league player, the Raiders earned the No. 3 seed in the tournament. After dispatching Lafayette in the first round, Colgate fell to Bucknell in the semifinals. Despite the loss, the Raiders recorded its second straight winning season with an 11-9 record.
In 2008-09 the women's team posted an 8-13 record, earning them the No. 5 seed in the conference tournament. The Raiders defeated No. 4 seeded Holy Cross in the first round to advance to the semi-finals where they fell to defending champ Army. Elise DeRose was named to the All-Patriot League First Team.
In 2009-10 the men's team finished with a 9-8 record and the women finished 9-7. Both teams finished in the top four in the Patriot League after regular season. The men beat No. one seeded Army for the second straight year in regular season while the women lost in Patriot League semifinals to Army. Michael Yassky, John Nogueras and Elise DeRose were named to the All-Patriot League second team .
During the 2010-11 season, the men's team finished with a 6-12 mark and made the quarterfinals of the Patriot League Tournament. Luke Gensburg was named rookie of the year after a 12-6 overall record at the top spot in singles and a 4-1 mark in conference play. The women reached the semifinals for the fifth-consecutive year with an upset win over fourth-seeded Lehigh in the quarters as the fifth-seed. Stephanie Bender was the lone postseason honoree as a second team All-Patriot League player. Pennington earned the Patriot League Award for Good Sporting Conduct.
In 2011-12, the men's team improved to nine wins and earned the fifth seed into the Patriot League Tournament. Gensburg was named first team All-Patriot League for the second-straight year. The women finished third in the league and made the Patriot League Semifinals for the sixth-consecutive year. The women defeated Bucknell for the first time in five years and Alex Petrini was named second team All-Patriot League. Pennington also reached his 100th career comibined victory with a win over St. Bonaventure at home.
The 2012-13 season saw Pennington coach the women to a great turnaround, finishing the year 12-6 and earn its seventh-straight appearance in the Patriot League Semifinals. The women started the year with a seven-match winning streak and Kelsey Shea was named Second-Team All-Patriot League. Pennington is now second all-time in women's victories. On the men side, the Raiders finished 7-11 and Luke Gensburg was named first team All-Patriot League for the third-consecutive year. Pennington now ranks third all-time in men's victories.
The 2013-14 men's squad was one of the most successful under Pennington, going 10-8 overall after posting a 7-11 mark the year before. They had big wins over Navy and Bucknell. It was the first time since 2006 Colgate had upended the Mids, while the Raiders beat Bucknell for first time since 2009. The men also improved its conference record with three more wins than in spring 2013. Individually, Luke Gensburg was named All-Patriot League First Team, becoming just third player in Colgate history to be named First-Team All-League all four seasons.
Prior to taking the job at Colgate, Pennington spent two years as head coach of the men and women's tennis teams at Juniata College in Huntingdon, Pa. In his two years with the Eagles, Pennington coached six all-conference selections and two league Rookies of the Year.
In the spring of 2006, he helped the men's team set a school record for wins in a season with 13 and in 2005, he guided the women to a 7-4 record after the squad recorded just one win the year before.
During his time at Juniata, Pennington founded the Attack & Defend tennis camp. Acting as camp director, Pennington helped instruct 50 children of all ages and ability levels.
While earning his master's degree at Clarion University, Pennington acted as the assistant coach of the women's tennis team from 2002-2004, taking a winless team to nine wins in just one year. He earned his degree in communications and mass media technology in 2004.
Outside of college tennis, Pennington has been the head tennis pro at Toftrees Resort and Conference Center and a ralley ball instructor at Blair Racquet Club. Pennington also spent time coaching boys and girls tennis at Hollidaysburg Area High School in 2001 and 2002.
He is also the director of the Colgate Nike Tennis Camps, which started in 2011. He is a member of the Hamilton Chapter of the Rotary Club.
Pennington during his collegiate student-athlete days was part of "The Streak" – one of the most amazing dynasties in collegiate athletics. Pennington's alma mater, Kalamazoo College in Michigan, has won 76 consecutive conference men's tennis championships dating to 1936 (no titles presented during World War II).
Pennington was captain his senior season of 2001 and part of an All-America doubles team with partner Andrew Minnelli. He was a Rolex ITA finalist in the fall of 2000 and ranked in the top 20 nationally in doubles. Pennington and the Hornets advanced all four years to the NCAA tournament. During his freshman year he helped the team clinch the bronze medal with a doubles win over Emory. The following year, Kalamazoo finished second in the country. In Pennington's final two years with the Hornets, the squad finished with matching ninth-place finishes.
His wife, Jenny Sue Pennington, teaches nutrition courses at Colgate. She was a snowboarding instructor and professional at Whiteface Mountain near Lake Placid for seven years, and the couple met there in 2010. They now have a daughter, Mia Shanley.
Get to Know 'Gate Athletics -- Bobby Pennington
"Bobby continues to recruit student-athletes who are exceptional on the tennis court and in the classroom. Both the men's and women's programs continue to exceed preseason Patriot League rankings and compete successfully with our peer schools. I have had the opportunity to know many Division I coaches, and Bobby is one of the most competitive and witty I have ever met." -- Victoria M. Chun, Director of Athletics.
Influential Person in My Career: My dad, Big Bob, took me to all my tournaments growing up.
An Idea or Invention I Wish I Had Thought of: Yogate.
What I Like About My Job: Coaching up our student-athletes and forming lifelong relationships.
What I Like About Competing: Cream always rises to the top, and winning.
What I Would Like to Change: Tennis getting more respect and love at the collegiate and national level.
What I Like That Would Surprise Those Who Know Me: I once was a Radio DJ and taught high school English.
What I Like About Myself: I beat to my own drummer and am loyal to close friends and family.
Heroes: Wife Jenny, Daughter Mia, Parents Bob and Janet, and Brother Michael.
Possession: Wristwatch from my dad.
Memento: Daughter Mia's paintings in my office
Magazines: Sports Illustrated and ESPN, subscriptions for both
Gadget: My Android LG3. NO iPHONE.
App: Bleacher Report.
Music: Rusted Root and 90s Rap.
Books: The Great Gatsby and Death of a Salesman.
Food: Middle Eastern and anything Jenny cooks.
Movies: Royal Tenenbaums and Big Lebowski.
Quote: "You only live once, but if you do it right, once is enough," by Mae West; and "Work Hard and Play Harder," by Tito Penny.