[4] In January 2007, like Robbie Neilson before him, MacDonald joined Scottish First Division club Queen of the South on loan to gain competitive experience.

[10] MacDonald established himself as Queens first choice keeper and was an integral part of the team on their run to their first ever Scottish Cup Final.

[11][15] On his return to Hearts, MacDonald said of his time at Queens, "My loan spell last year was good and allowed me to play in big games like the Scottish Cup Final.

"[16] Queens attempted to bring Macdonald back for a third loan spell in December 2008 but Hearts turned them down as he had now made his first team debut for the club.

[17] MacDonald returned to Hearts for the 2008–09 season and, after playing regularly during pre-season fixtures, new manager Csaba Laszlo stated his intent to use him as back-up to first choice keeper Steve Banks.

Hearts lost the game 2–0, the second goal a last minute penalty from Kris Boyd, who had scored twice against MacDonald in the 2008 Scottish Cup Final.

[20] Manager Laszlo said that he was happy with MacDonald's performance against Rangers but he then dropped him in favour of Slovakian loan signing Marian Kello.

[22] He made his European debut on 25 August 2011 against Tottenham at White Hart Lane, conceding a penalty when he felled Harry Kane inside the box.

[32] MacDonald helped the club reach the Scottish League Cup final after beating Inverness Caledonian Thistle in the semi-final, winning 5–4 in a penalty shootout following a 1–1 draw.

[42] MacDonald established himself as the number one keeper at Falkirk, and started every single league game of the 2014–15 Scottish Championship campaign.

[45] On 13 September 2019, MacDonald joined Championship club Alloa Athletic on an emergency loan, following an injury to first choice goalkeeper Neil Parry.

[48][49] On 24 July 2024, Hearts announced MacDonald had returned to the club to play for their B team in the Lowland Football League.