In 2006, Beckett succeeded David Elsworth at Whitsbury Manor Stables, near Fordingbridge, Hampshire. In the next five seasons, he saddled over 240 more winners, including his first British Classic winner, Look Here, in the Oaks in 2008. In 2010, Beckett purchased his currrent base, Kimpton Down Stables in nearby Andover, and completed his move in time for the start of the 2011 season. Since then, he has saddled two more British Classic winners, Talent in the Oaks in 2013 and Simple Verse in the St. Leger in 2015; the latter also won the British Champions Fillies & Mares Stakes at Ascot the following month to give Beckett the fourth Group 1 victory of his career.
Beckett took his career tally to 1,000 winners when the 6-year-old Another Boy won an apprentice handicap at Salisbury in August, 2019. In 2020, he enjoyed his most successful season so far, numerically, passing the landmark of a hundred winners on British soil for just the second time.