Career
Early career
Having been on the books of Hemel Hempstead Town as a youth player, Calcutt began his senior career with Berkhamsted, where he quickly gained a reputation as an exciting prospect, producing a 2013-2014 tally of 41 goals from 52 appearances in all competitions. In the second-half of that season, he joined Saint Albans City as a dual-registration player, but only turned out for the side on one occasion. Towards the end of the season, he had a trial with Millwall.
Stevenage
Calcutt joined League Two club Stevenage on trial terms ahead of the 2014-2015 season.
As is customary for trialists, he was initially unnamed by the club, however an impressive goal in a home friendly against Premier League side West Ham United led to a campaign by Sky Sports to find the mystery goalscorer. He finally signed a contract with Stevenage on 9 August, making his Football League debut that same day as a late substitute at home to Hartlepool United.
Calcutt"s first professional goal came in only his second League appearance away at Plymouth Argyle in a 1-1 draw, where he came on at half time for the injured Darius Charles. = Wealdstone (loan) Calcutt moved on a month"s loan to Conference South side Wealdstone on 24 October 2014.
Wealdstone
In the summer of 2015, Calcutt returned to Wealdstone on a permanent basis.