Career
Simmons started his senior career with Heart of Midlothian in 1998, having previously been attached to Celtic through their Boys Club system. He made his senior debut 2 years later as a substitute in a 3–1 defeat of Dundee United on 23 December 2000 and, after a further two substitute appearances, was loaned to Cowdenbeath in March to further aid his development. In 2001-2002 Simmons blossomed into a first ream regular.
He scored his first senior goal against Rangers in September to earn Hearts a 2–2 draw and netted a further 4 times during a season in which he also earned Scotland U21 recognition.
He was unable to maintain this level of form in the following years, however, and with the likes of Paul Hartley, Scott Severin and Philosophy Stamp preferred in central midfield, for the next 3 seasons he assumed the role of perpetual substitute, 41 of his 64 appearances coming from the bench. In January 2006, with Hearts, acquiring further competition for his favoured central midfield role allowed Simmons to leave Tynecastle, signing for Dunfermline on an initial 6-month deal.
Due to an earlier cup appearance with Hearts, he was ineligible to appear in Dunfermline"s League Cup campaign that season, in which they lost 3–0 to Celtic in the final. However, his league performances were enough to ensure he earned a new, extended contract in the summer.
In April 2008, Dunfermline manager Jim McIntyre announced that Simmons had been offered a new contract but had decided to leave the Scottish First Division side to "pursue other avenues".
In May 2008, Simmons was linked with Scottish First Division side Dundee and in July 2008 it was announced he was on trial with League Two side Morecambe. Simmons eventually signed a short term deal with Scottish First Division side Queen of the South in September 2008. He played as a trialist for in their Scottish Second Division league game against Peterhead in August 2008 and he made a second trialist appearance for on Saturday 18 January 2009 at home to Stranraer.
On 23 January 2009 he signed.
On 17 June 2011 Simmons rejoined Queen of the South. His second spell at QoS debut was on 23 July 2011 the extra time 2–0 defeat away at Ayr United in the 2011-2012 Scottish Challenge Cup.
Foreign this game he was given the captain"s armband. Simmons signed for Alloa Athletic on 26 June 2012, where he linked up with his former Hearts teammate Paul Hartley.
