Sherwood's younger brother, Simon, was a successful jockey best noted for winning the 1989 Cheltenham Gold Cup on Desert Orchid.
Some of the most famous horses he has trained over the years include: Arctic Call, Be Rude Not To, Claymore, Coulton, Cruising Altitude, Eric’s Charm, Him Of Praise, Hulysse Royal, Jaunty Flight, Large Action, Lord Of The River, Manorson, Mischievous Milly, Monkerhostin, Puffin Billy, Tildarg, The Breener, The West Awake and Young Snugfit.
Festival victories include: Aldino, Coulton, Rebel Song, The West Awake and Young Pokey.
Sherwood trained four of the Mares Final (Newbury) winners: Atrabates (1986), Northern Jinx (1989), Jaunty Flight (2008) and Argento Luna (2009).
Tarnya also had a love for horses, being a National Hunt jockey before meeting Oliver, riding winners as a professional under rules.