He previously played in the National Hockey League (NHL) with the Detroit Red Wings, Boston Bruins, New York Islanders, Toronto Maple Leafs, and the Calgary Flames.

In 17 games, he recorded only three wins, but continued to work on his style and play, impressing the coaching staff in the process[citation needed].

The Ontario Hockey League then came calling the following season and MacDonald began play for the Peterborough Petes as their starting goaltender.

He remained the Pete's starting goaltender until the 2001–02 season when he joined the Toledo Storm of the ECHL after signing with the Detroit Red Wings as a free agent.

The 2005–06 AHL season saw an influx of goaltenders into the Red Wings farm system and MacDonald competed to stay near the top.

MacDonald was brought up to the NHL for the 2006–07 season when he was named as a backup goaltender to Dominik Hašek and Chris Osgood of the Detroit Red Wings.

Many Islanders fans were apprehensive about this arrangement, feeling that MacDonald may not be ready to be DiPietro's backup on a regular basis- especially since they hoped their starting netminder was going to get more time to rest.

He remained with the Red Wings for the final months of the regular season and playoffs as Jimmy Howard's backup due to an injury to Chris Osgood.

He was their backup goaltender behind Karri Ramo[11] MacDonald was signed as a free agent on July 1, 2014 by the Montreal Canadiens to a one-year two-way contract.

[12] MacDonald failed to make the Canadiens out of training camp and, after clearing waivers, was assigned to their AHL affiliate, the Hamilton Bulldogs.