Career
Cregg is a midfielder. Cregg has previously played for Arsenal, Falkirk, Hibernian, Greenock Morton, Street Mirren, Bury and Street Johnstone. He also represented the Republic of Ireland at youth international levels.
Cregg started his senior career at Arsenal.
His first senior appearance was in a 3-1 victory against Everton in the League Cup on 9 November 2004, as an 89th-minute substitute for Arturo Lupoli. In all he made three appearances, all of them being in the League Cup.
Cregg joined Scottish Premier League club Falkirk in January 2006 and made over 100 Scottish Premier League appearances for the club He was released in the summer of 2009, having made his last appearance for the club in the 2009 Scottish Cup Final.
After his release by Falkirk, Cregg signed for Hibernian.
Cregg followed manager John Hughes in making that move. Cregg left Hibs at the end of the season. Cregg then played in a reserve team friendly match for Shamrock Rovers against Manchester United.
Cregg then played as a trialist for Greenock Morton in a Scottish First Division match against Ross County on 25 September 2010.
The Greenock Telegraph reported on 1 October 2010 that Cregg had turned down a contract offer from Morton to sign for their Renfrewshire derby rivals Street Mirren. Cregg signed for the Paisley club, agreeing a contract until January 2011.
Cregg signed a one-year contract with Bury in August 2011. In May 2012, Cregg was released by the club after being deemed surplus to requirements.
Cregg played for Street Johnstone as a trialist in July 2012 and then agreed a one-year contract with the club
In August 2014 Cregg signed a contract until the end of the season with League of Ireland side Shamrock Rovers. International
While he was at Arsenal, Cregg became a regular in the Republic of Ireland under-19 team He later represented the Republic of Ireland national under-21 football team