His players have been named all-league 22 times and have earned seven Player of the Month awards. He has coached both a Patriot League Player of the Year and Rookie of the Year. Pennington also serves on the ITA Division I Men's Northeast Rankings Committee.
The past four years he has coached Luke Gensburg, who is only the third player in Colgate history to be named First Team All-Patriot League all four seasons.
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.
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.
This past year in 2012-13, Pennington coached the women to a great turnaround to finish 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.
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.
A 2001 graduate of Kalamazoo College, 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 University. 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. He captained the team during his senior year, excelling in doubles play. He was a doubles finalist at the Midwest Rolex Championship and was ranked in the top 20 nationally as a doubles player in the fall of 2000.
Pennington resides in Hamilton with his wife, Jenny and their daughter Mia.