Complex sentence: After failing to make a significant breakthrough into the Middlesbrough side, Hudson was sold to Chesterfield in 2003 and after having a small loan period there and at Carlisle United, made a name of himself as a central midfielder at the Spireites.
Split into simpler sentences: After failing to make a significant breakthrough into the Middlesbrough side, Hudson was sold to Chesterfield in 2003 after a short loan period there and at Carlisle United. He subsequently made a name of himself as a central midfielder at the Spireites.