Rosslee enjoyed success as a player with Cape Town Spurs, Hellenic and Santos. He made his league debut for Cape Town Spurs in 1990 and retired in 2004 due to several shoulder injuries. Rosslee was ranked among the better defenders of his time in South Africa but was not capped at international level for South Africa.
He linked up with Ajax CT as a junior coach, eventually becoming the head of the club's youth development programme and had short uneventful stints in lower divisions but can claim fame in the hot seat for his excellent run to the last eight of the prestigious ABSA Cup with the youthful Ajax reserve team before they narrowly lost to Silver Stars.
In 2007, he was appointed coach of Ajax CT.
He became the fourth manager of Moroka Swallows in March 2015, little over two months before the end of the 2014–15 season, but was unable to save them from their first ever relegation from the top division.
In 2016, Rosslee was appointed as the technical director of Cape Town City FC. He also operates as the Head Coach of the club's reserve team.
- Abrahams, Farouk (25 June 2007). "Rosslee lined up as next Ajax coach". Independent Online. Retrieved 10 November 2010.
- "Craig Rosslee And Ajax Cape Town Part Ways". goal.com. 13 May 2009. Retrieved 10 November 2010.
- Pedroncelli, Peter (8 September 2009). "Craig Rosslee Joins Orlando Pirates As Assistant Coach". goal.com. Retrieved 10 November 2010.
- "Two-and-a-half-years for Rosslee". 30 November 2012. Retrieved 30 November 2012.
- "Moroka Swallows' relegation a historic one in South Africa". ESPN FC. 2 June 2015. Retrieved 2 June 2015.
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