[6] He scored his first league goal for the club in a 1–1 draw at St Mirren Park against Dundee United on 26 January 2011, netting a header from a well placed corner kick by Steven Thomson.

He then scored his second league goal for the club in a 3–3 draw against Inverness Caledonian Thistle on 12 February 2011, with a header from a Jure Travner corner.

During a match against Dundee United in the SPL on 6 August 2011, McGregor suffered cruciate ligament damage that prevented him from playing for most of the 2011–12 season.

[7] The injury sidelined McGregor for the rest of the 2012–13 Scottish Premier League season, and meant that he had only played 12 competitive matches for the club in a two-season period.

During pre-season of season 2013–14, McGregor returned to action after recovering from his second cruciate ligament injury, and admitted that he feared he may never play football again.

He made his debut for Rangers when he came on as a 92nd-minute substitute for Richard Foster in the opening game of the Scottish Championship season against Hearts.

[23] He retired from playing at the end of the 2022–23 season (in which he was an unused substitute for 13 league fixtures), and became head coach of the Hibs under-18 team.