In 1997 he won the
Australian Open boys' doubles title with fellow Brit
James Trotman. They defeated South African pairing Jaco van der Westhuizen and
Wesley Whitehouse 7–6, 6–3 in the final. Sherwood, won futures tournaments in Wrexham and Edinburgh, and also reached the semi-final in Mulhouse and the final in Plaisir, France. By 2003, Sherwood had acquired a reputation for a lackadaisical attitude, a party loving life style and negatively influencing younger players. While at a Jamaica Futures event in November 2003, Sherwood delivered an on-court barrage at his
Lawn Tennis Association coach. Back in the UK, he missed a training session claiming he was ill, despite living five minutes away from the LTA's headquarters with an on-site doctor. Next day, the LTA's team manager
Mark Petchey expelled him from the LTA. With the support of his parents, Sherwood put his tennis career back on track. By November 2004, Mark Petchey was funding his coaching throughout the winter. to help Great Britain win 3–2. He entered the singles at
Wimbledon in 2005, and defeated
Ricardo Mello in the first round{{cite news |title=Briton Sherwood lands famous win In September 2005, at the
World Group Play-off against Switzerland, Sherwood was beaten in the first singles dead rubber, with Great Britain losing 5–0. Since retiring from playing in 2008, Sherwood became a nationally recognised
Lawn Tennis Association coach, coaching top performance players in the country. ==ATP Challenger and ITF Futures finals==