The Middlebury College men's tennis team sent several players over the mountain to Dartmouth for the 2009 Dartmouth Shootout Men's Tennis Tournament. Seven eight-man singles draws were played, as well as three eight-man doubles brackets.

Senior Peter Odell (Scarsdale, N.Y.) captured the "B" singles draw, winning the semifinal 3-6, 7-6 (8), (5) before taking the title by default. Odell also captured the "C" doubles flight with his partner Mike Malhame (Douglaston, N.Y.), earning 9-7, 8-5 and 8-5 victories.

Sophomore Derrick Angle (Troy, N.Y.) advanced to the finals in the "C" bracket, junior Jeronimo Riefkohl (Munich, Germany) did the same in the "F" draw, while sophomore David Farah (Flint, Mich.) advanced to the finals of the "G" flight. Winning the "G" flight was senior Chris Mason (Owings Mills, Md.), who topped Farah 6-1, 6-1 in the finals.