[3][4] After attending Stonyhurst College in Lancashire, Wooldridge trained at the London Academy of Music and Dramatic Art, then assisted directors including Alan Ayckbourn, Eric Thompson, Frank Hauser and Michael Blakemore.
In the first ten years of his career he directed more than sixty productions in London and throughout the UK, by authors including Alan Ayckbourn, René de Obaldia, Pam Gems and Athol Fugard.
The production has featured amongst others Michael Ball, Brent Barrett, Len Cariou, Glenn Close, Michael Crawford, Kerry Ellis, David Essex, Maria Friedman, Joel Grey, Brian May, Caroline O'Connor, Adam Pascal, Philip Quast, and Sally Ann Triplett, and the works of Cy Coleman, George and Ira Gershwin, Lerner and Lowe, Tim Rice, Alain Boublil and Claude-Michel Schönberg, Stephen Sondheim, and songs from the productions of Richard Eyre, Nicholas Hytner, Cameron Mackintosh, Trevor Nunn, Tim Rice and Andrew Lloyd Webber.
In 2018, along with his international masterclass and teaching commitments, Hugh Wooldridge directed Play on Words – a celebration of PG Wodehouse and his fellow Wordsmiths on Broadway – with Hal Cazalet at Live at Zedel/Crazy Coqs and in New York;[15] and another production of Jesus Christ Superstar at Teatru Astra, Gozo/Malta.
[16] In 2019, Hugh Wooldridge produced and directed The Best of Rock Musicals, hosted by Tim Rice, Christopher Biggins and Richard O’Brien at the Eventim Apollo, Hammersmith for the benefit of the suicide awareness charity, The Charlie Waller Trust.