A summary of the results of the Alumni Race.
Open competition
Open competition for the King Henry VIII School Old Boys' Trophy.
| Year | 1st | 2nd | 3rd | Race Winner |
| 2008 | Sedbergh | Sherborne | Winchester | J McMullan (Charterhouse) |
| 2007 | Winchester | Sedbergh | Ampleforth | S Wurr (Warwick) |
| 2006 | Winchester | Sedbergh | Sherborne | A Symonds (Sedburgh) |
| 2005 | Winchester | Sedbergh | Sherborne | B. Moreau (Winchester) |
| 2004 | Winchester | Sedbergh | Harrow School | B Moreau (Winchester) |
| 2003 | Sedbergh | Winchester | Dulwich | A Symonds (Sedburgh) |
| 2002 | Winchester | Sedbergh | Dulwich | C Sykes (Sedburgh) |
| 2001 | Winchester | Sedbergh | Charterhouse | E Barnett (Winchestar) |
| 2000 | Winchester | Sedbergh | Dulwich | R Wates |
| 1999 | Winchester | Sedbergh | Denstone | C Sykes (Sedburgh) |
| 1998 | Winchester | Sedbergh | Harrow School | C Sykes (Sedburgh) |
| 1997 | Dulwich | Charterhouse | Winchester | L Bulson (Dulwich) |
| 1996 | Dulwich | Denstone | Charterhouse | L Bulson (Dulwich) |
| 1995 | Dulwich | Sedbergh | Denstone | L Bulson (Dulwich) |
| 1994 | Dulwich | Winchester | Denstone | J Rye (Dulwich) |
| 1993 | Dulwich | Denstone | Winchester | J Rye (Dulwich) |
| 1992 | Dulwich | Oubdle | Charterhouse | J Watson (Dulwich) |
| 1991 | KH VIII | Dulwich | Denstone | N Cowie (KH VIII) |
| 1990 | Dulwich | Denstone | Winchester | J Watson (Dulwich) |
| 1989 | KH VIII | Winchester | Dulwich | N Cowie (KH VIII) |
| 1988 | KH VIII | Harrow County | Dulwich | N Cowie (KH VIII) |
| 1987 | Marlborough | Dulwich | KH VIII | P O'Brien (Harrow County) |
| 1986 | KH VIII | Bradfield | Brentwood | J Watson (Dulwich) |
| 1985 | KH VIII | Shrewsbury | Dulwich | J Watson (Dulwich) |
| 1984 | KH VIII | Bradfield | Brentwood | D Glassborow (KH VIII) |
| 1983 | KH VIII | Dulwich | Shrewsbury | N Cowie (KH VIII) |
| 1982 | KH VIII | Harrow County | KCS Wimbledon | N Cowie (KH VIII) |
| 1981 | KH VIII | Harrow County | Denstone | P O'Brien (Harrow County) |
| 1980 | KCS Wimbledon | KH VIII | Harrow County | R D Robinson (KCS Wimbledon) |
| 1979 | KH VIII | Abingdon | Sevenoaks | N D B Dorey (Marlborough) |
| 1978 | Harrow County | KH VIII | Denstone | R Heat (Harrow County) |
| 1977 | Marlborough | Harrow County | KH VIII | N D B Dorey (Marlborough) and N Pritchard (Winchester) |
| 1976 | Leighton | Shrewsbury | Harrow County | J P Valentine (KCS Wimbledon) |
| 1975 | Denstone | KH VIII | Bradfield | M H Wells-Cole(Bradfield) |
| 1974 | Westminster | Rugby | Denstone | J G Forrest (Westminster) |
| 1973 | Denstone | KH VIII | Rugby | J H Brearley (Sedberg) |
| 1972 | Denstone | Rugby | KH VIII | A R Barrington (Denstone) |
| 1971 | Denstone | KCS Wimbledon | KH VIII | A R Barrington (Denstone) |
| 1970 | Rutlish | Denstone | Merchant Taylors | J Booth (Leigton Park )and S H James (Kingswood) |
| 1969 | Merchant Taylors | Denstone | KH VIII | T J Briault (Laytmer Upper) |
| 1968 | Rutlish | KCS Wimbledon | Merchant Taylors | M L Barratt (Laytmer upper) and D M Turner (Liverpool College) |
| 1967 | KCS Wimbledon | St Edwards | KH VIII | J P Valentine (KCS Wimbledon) |
| 1966 | KCS Wimbledon | KH VIII | Wellington | M L Barratt and T U Briault (Laytmer upper) |
| 1965 | KCS Wimbledon | St Edwards | Denstone | R D Robinson (KCS Wimbledon) |
| 1964 | KCS Wimbledon | Rutlish | Haberdashers | R D Robinson (KCS Wimbledon) |
| 1963 | Wellington | Lancing | KCS Wimbledon | M B S Tulloh (Wellington) |
| 1962 | Wellington | Rutlish | KCS Wimbledon | C H Llewellyn Smith and M B S Tulloh (Wellington) |
| 1961 | Rutlish | Haberdashers | KCS Wimbledon | R E Bell (St Dunstans) |
| 1960 | Rutlish | KCS Wimbledon | Bradfield | R E Bell (St Dunstans) |
| 1959 | Rutlish | KCS Wimbledon | Bradfield | R E Bell (St Dunstans) |
| 1958 | Repton | Bradfield | Shrewsbury | M Berisford (Repton) |
| 1957 | Bradfield | Shrewsbury | Rutlish | T P Hicks (Bradfield) |
| 1956 | Repton | Charterhouse | Bradfield | M Berisford (Repton) |
| 1955 | Charterhouse | KCS Wimbledon | Repton | M Berisford (Repton) |
| 1954 | KCS Wimbledon | Charterhouse | Dunstans | B F C Sennitt (Charterhouse) |
| 1953 | Uppingham | Charterhouse | Repton | R M Newey (Repton) |
V40 competition
Veterans 40 competition for the Old Brentwood's Trophy.
| Year | 1st | 2nd | 3rd | Race Winner |
| 2008 | Winchester | Westminster | Charterhouse | D Symons (Bournemouth) |
| 2007 | Dulwich | Winchester | Charterhouse | C Finill (Harrow County) |
| 2006 | Winchester | St George's Weybridge | Dulwich | C Finill (Harrow County) |
| 2005 | Dulwich | Winchester | Westminster | C Finill (Harrow County) |
| 2004 | Winchester | Charterhouse | Westminster | C Finill (Harrow County) |
| 2003 | Westminster | Charterhouse | Dulwich | J Danahay (Denstone) |
| 2002 | Dulwich | Wesminster | Brentwood | J Danahay (Denstone) |
| 2001 | Winchester | Wesminster | Charterhouse | C Finill(Harrow County) |
| 2000 | Charterhouse | Winchester | Harrow County | J Watson (Dulwich) |
| 1999 | Charterhouse | Wesminster | Dunstone | C Finill (Harrow County) |
| 1998 | Charterhouse | Dulwich | Denstone | H Arnold (Charterhouse) |
| 1997 | Dulwich | Charterhouse | Sherbourne | J Rye (Dulwich) |
| 1996 | Dulwich | Winchester | Sherbourne | H Arnold (Charterhouse) |
| 1995 | Dulwich | Denstone | Winchester | S Ingall (Oundle) |
| 1994 | Dulwich | Winchester | | J Rye (Dulwich) |
| 1993 | Westminster | Denstone | | H Arnold (Charterhouse) |
| 1992 | Bradfield | Denstone | | T Pailthrope (Brentwood) |
| 1991 | Bradfield | | | H Arnold (Charterhouse) |
| 1990 | Dulwich | Bradfield | | H Arnold (Charterhouse) |
| 1989 | Bradfield | | | T Pailthrope (Brentwood) |
| 1988 | Dulwich | | | K Spaicie (Queen Elizabeth School) |
| 1987 | Bradfield | Brentwood | | M B S Tulloh (Wellington) |
| 1986 | Brentwood | Bradfield | | J Hancock (Dulwich) |
V50 competition
Veterans 50 competition for the Chataway Cup.
| Year | 1st | 2nd | 3rd | Race Winner |
| 2008 | Winchester | Westminter | Charterhouse | R Pitt (Charterhouse) |
| 2007 | Westminster | Charterhouse | Sherborne | R Pitt (Charterhouse) |
| 2006 | Westminster | Kent Coll. Canterbury | Winchester | S Ingall (Oundle) |
| 2005 | Westminster | Winchester | Dulwich | G Ball (Westminster) |
| 2004 | Westminster | Winchester | Charterhouse | R Pitt (Charterhouse) |
| 2003 | Westminster | Sherborne | Winchester | R Barrington (Denstone) |
| 2002 | Westminster | Denstone | Dulwich | G Ball (Westminster) |