The Timothy S. Scott Bowl
Choate Rosemary Hall is one of six schools that compete annually for the Timothy S. Scott Bowl, a trophy recognizing the strongest varsity boys' cross country team--based on dual meet records--from among the following historical rivals in Connecticut: Choate Rosemary Hall, Hotchkiss School, Kent School, Kingswood-Oxford School, Loomis Chaffee School, and Taft School.
The Scott Bowl is named for the former Kent School coach whose undefeated 1973 team donated the trophy. Some teams also have referred to this trophy as the "Kent Bowl" over the years.
In the fall of 2013, the Wild Boars claimed the Scott Bowl for a record seventeenth time.
Timothy S. Scott Bowl Champions
| 1973 | Kent School |
| 1974 | Loomis Chaffee School |
| 1975 | Choate Rosemary Hall |
| 1976 | Loomis Chaffee School |
| 1977 | Loomis Chaffee School |
| 1978 | Loomis Chaffee School |
| 1979 | Choate Rosemary Hall |
| 1980 | Loomis Chaffee School |
| 1981 | Loomis Chaffee School |
| 1982 | Kent School |
| 1983 | Taft School |
| 1984 | Choate Rosemary Hall |
| 1985 | Choate Rosemary Hall |
| 1986 | Choate Rosemary Hall |
| 1987 | Hotchkiss School |
| 1988 | Loomis Chaffee School |
| 1989 | Taft School |
| 1990 | Taft School |
| 1991 | Taft School |
| 1992 | Choate Rosemary Hall |
| 1993 | Loomis Chaffee School |
| 1994 | Loomis Chaffee School |
| 1995 | Loomis Chaffee School |
| 1996 | Hotchkiss School |
| 1997 | Choate Rosemary Hall |
| 1998 | Choate Rosemary Hall |
| 1999 | Choate Rosemary Hall |
| 2000 | Choate Rosemary Hall |
| 2001 | Loomis Chaffee School |
| 2002 | Choate Rosemary Hall |
| 2003 | Choate Rosemary Hall |
| 2004 | Loomis Chaffee School |
| 2005 | Choate Rosemary Hall |
| 2006 | Loomis Chaffee School |
| 2007 | Choate Rosemary Hall |
| 2008 | Taft School |
| 2009 | Choate Rosemary Hall |
| 2010 | Choate Rosemary Hall |
| 2011 | Loomis Chaffee School |
| 2012 | Loomis Chaffee School |
| 2013 | Choate Rosemary Hall |