As a schoolboy he played football for Parkway Youth Club, alongside fellow future professional player Marcus Stewart, and for Backwell United, and was invited to join the Bristol Rovers youth team for a tournament in Germany. After losing in the final, Gill and his Rovers teammates indulged in the local beer to the extent that they were arrested and kept in police cells overnight. At the age of 16 he joined Trowbridge Town, then playing in the regional divisions of the Southern League (level 7 of the English football league system) under the management of Ken Knighton. The young Gill was spotted by Frank Clark, who had worked with Knighton at Sunderland and succeeded him as Leyton Orient manager, and Clark signed Gill on an 18-month contract in 1988. However, he found it difficult to settle – "moving to the east end of London from a small village was a real culture shock for me" – and returned to the West Country at the end of his contract without featuring for the Orient first team. In December 1990, after a brief stint with Weston-super-Mare, Gill joined Bath City, newly promoted to the Conference. In his first 18 months with the club he appeared only infrequently for the first team, but in the 1992–93 season he established himself as a first-team player and remained so for the duration of his Bath City career. In all he spent six seasons with the club on a semi-professional basis, playing part-time while working as a representative for a supplier of pitch care products, and made 218 appearances for the club in all competitions, scoring 14 goals. He helped the club reach the third round of the 1993–94 FA Cup, in which they held First Division club Stoke City to a goalless draw at Stoke before losing the replay 4–1. Since 1986, Bath City had drawn a significant amount of income from allowing Football League club Bristol Rovers to share their Twerton Park ground; Rovers' return to Bristol at the end of the 1995–96 season meant that savings needed to be made, including cuts in the playing budget. Together with teammate Rob Cousins, Gill joined local rivals Yeovil Town for the 1996–97 season for a fee of £9,500. Though Yeovil were at the time in the Isthmian League Premier Division, the level below the Conference, under player-manager Graham Roberts they were playing good football and were expected to challenge for promotion. Gill scored 16 goals in all competitions playing in central midfield, and was capped for the England National Game XI, England's representative team for semi-professional footballers, against an Ireland B team in Dublin.