After spending time in Luton Town's youth system, McGuinness joined Football Conference side Rushden & Diamonds where he made five appearances during the 2008–09 season.
[1] In 2012, McGuinness moved to the U.S. and joined PDL side VSI Tampa Flames where he made 16 appearances and scored his only goal of the year in the season opener on 6 May which ended in a 4–2 defeat to Ocala Stampede.
[3] On 5 February 2013, McGuinness signed with newly formed USL Pro side VSI Tampa Bay FC.
[4] He made his debut on 1 June as a substitute in an inter-league match with the Portland Timbers Reserves which ended in a 4–4 draw after Tampa Bay conceded three unanswered goals in the second half.
[5] On 23 January 2015, it was announced that McGuiness that was the second player on the squad of Colorado Springs Switchbacks FC[6] McGuinness was announced on 14 April 2016 as a member of the initial roster for the Tampa Bay Rowdies' NPSL reserve side Rowdies 2.