When Villas-Boas was dismissed on 4 March 2012 and Roberto Di Matteo was appointed caretaker manager of Chelsea, Holland filled the role of assistant manager. He continued in this position under the interim manager Rafael Benítez.
When Villas-Boas left his position on 4 March 2012, Roberto Di Matteo became the temporary manager of Chelsea. As a result, Holland filled the role of deputy manager and remained in this capacity under the supervision of interim manager Rafael Benítez.