Thanks to the newly introduced flat draws, Calabrese was able to qualify for the venue stages of his debut tournament, the Wuxi Classic, as he defeated Anthony McGill 5–3. He lost 5–1 to John Higgins in the last 64 at the venue in China.&lt;ref name="2013/14"&gt;&lt;/ref&gt; At the UK Championship he led world number 22 Dominic Dale 5–2, but was pegged back to 5–5 with Calabrese saying afterwards that he couldn't hold himself together. However, in the deciding frame he made a composed 70 break to win 6–5 before losing 6–3 against Gary Wilson in the second round. Calabrese was knocked out of the first round of seven of the eight European Tour events, but at the Bluebell Wood Open he defeated world number two Mark Selby 4–2, Dechawat Poomjaeng 4–2 and David Morris 4–1 and then led Jimmy Robertson 3–0 in the last 16, but was beaten 4–3. He finished his debut season on the tour ranked world number 105.