Cropper was a produce of the youth setup at
Sheffield Wednesday and signed professional terms with The Owls in August 2000, a few months prior to the club's relegation from the
Premier League. He would make the first and reserve teams and although offered a new deal he left the club on a free transfer in the summer of 2002. During the 2001–02 season Cropper signed on loan for
Worksop Town, He notched up a decent scoring rate for them, netting ten goals in twenty games. On 10 May 2002, Cropper along with
Ben Futcher became
Lincoln City manager
Keith Alexander's first signings of his second spell in charge at
Sincil Bank. He made his
Football league debut in the club's 1–1 opening day draw at
Kidderminster Harriers on 10 August 2002, though this was marred when, seven minutes from time, referee Phil Crossley deemed his challenge on
Abdou Sall unfair and, following an earlier booking for dissent, dismissed him for two bookings. His home debut, three days later, was a far happier affair as he notched his first goal for the club in a 2–0 victory over
Rochdale. Cropper had a good season with Lincoln, but failed to score as many goals as his play deserved in a season which saw him and his team lose out in the playoff finals at the
Millennium Stadium. The following season, Cropper found himself overlooked, and was finding himself on the bench on a regular basis due to long lay offs with injury and the performances of the club's other forwards. In February 2004 he signed on loan with Non-League club
Gainsborough Trinity, in a month that saw him net once in five appearances at
The Northolme. He returned to Lincoln after his month and was subject to another loan offer, this time from
Scarborough, but he rejected the chance to play for Scarborough in favour of a permanent switch to local rivals
Boston United. Cropper played five times for Boston and scored once but suffered a serious knee injury towards the end of the season which prompted his release from the club. Upon returning to the game Cropper turned down a move to
King's Lynn before re-joining former club Worksop Town. He made a move to
Matlock Town in September 2005 for an undisclosed fee. He joined Woolley Moor United ahead of the 2011–2012 season, debuting in the club's 4–2 Midlands Regional Alliance, Division 1 victory at Findern on 13 August 2011. ==Personal life==