A total of sixteen players have turned out for The Silkmen and The Pilgrims over the years and ahead of tomorrow afternoon's Sky Bet League Two encounter at Home Park, we take a look at some of these.
Defender Tony started his career at Stockton Town, before progressing through the youth ranks at Hartlepool United.
He joined Stockport County in July 1990, yet it was at York City where he really made a name for himself - amassing over two-hundred appearances for The Minstermen, scoring fifteen times.
Moves to Reading and Walsall followed and it was during his time with the latter of these that he completed a short loan move to Plymouth Argyle.
Tony signed for Notts County in August 2003 and subsequently made the move to the Moss Rose in July 2004.
His time with The Silkmen was injury-plagued, yet he did play an integral part in Brian Horton's p[lay-off reaching side of 2005.
Tony concluded his career with spells at FC Halifax Town, Staybridge Celtic and New Mills.
Nathan started his career at Staffordshire University and Kidsgrove Athletic, before signing for Kidderminster Harriers in August 2012.
Numerous loan spells ensued, before Bristol Rovers acquired his services on a permanent basis in January 2015.
After securing promotion with The Pirates, Nathan then completed short-term moves to Tranmere Rovers and Lincoln City respectively - before signing for Torquay United in January 2016.
Nathan made forty-one appearances for The Gulls - scoring twelve goals, before he made the move to Plymouth Argyle in January 2017 for £50,000.
Twelve months later, Nathan joined John Askey's illustrious Silkmen side which went on to secure the National League title.
The striker would play a crucial part in that incredible achievement and was an ever-present in the side following his move.
Nathan scored five goals for the club during the 2017/18 season and who can forget his last-gasp effort against Gateshead which handed Macc another defiant victory on our way to regaining our EFL status.
Signing permanently in the summer of 2018, Nathan struggled to re-create his form of the previous season and made the switch to Solihull Moors the following December for an undisclosed fee.
Simon was one of eight pre-season signings in the summer of 1999, as Sammy McIlroy plotted an immediate return to the third tier.
Defender Collins had already amassed well over one-hundred appearances for Huddersfield Town and Plymouth Argyle before arriving at the Moss Rose and brought a wealth of experience to the side.
He was a strong and powerful centre-half, who was good in the air and gave his all every single week.
A knee injury plagued his second season at the club however and he subsequently completed a loan move to Shrewsbury Town.
Released the following summer, Simon concluded his career by turning out of an array of non-league sides.
Richard entered the professional game at the age of twenty-three, when he signed for Plymouth Argyle in January 1994.
After eighteen months at Home Park, Richard signed for Stockport County for £50,000 and became a fans favourite with The Hatters.
Richard enjoyed a brief loan spell at the Moss Rose in January 1997, before seeing-out the 1996/7 campaign at Rotherham United.
Landon then signed a permanent deal with The Silkmen in the summer of 1997 and will be best remembered by the Moss Rose faithful for scoring the second (and decisive goal) in our inaugural Football League match against Torquay United.
First team appearances proved to be hard to come by for Richard however and he was released in the summer of 1999.
He went on play for Hednesford Town, Altrincham and Radcliffe Borough, before returning to Stockport as their Kitman.
Six-foot midfielder Luke began his career with Plymouth Argyle, earning a professional contract in 2005 aged 18. His career started brightly, with manager Ian Holloway praising his “fine touch” and talent. In 2007 he was named by The Guardian in the ten best prospects to watch out for.
It was during his time with Plymouth that Luke spent a short time out on loan with Leyton Orient. Initially joining for a month period, he ended up staying for three and made a total of fourteen appearances.
Luke eventually left Plymouth in 2011, moving first to Cheltenham Town and then on to Shrewsbury, York and Grimsby.
It was whilst at Grimsby that he came to the Moss Rose on loan, making eighteen appearances and scoring a number of important goals, the most memorable in the FA Trophy match against Dulwich Hamlet where he found the net twice.
Although he had impressed all round at Macclesfield he returned to Grimsby in the summer of 2017 and was subsequently released.
He is currently plying his trade with Wrexham in the National League.
Honourable mentions: John Barnett, Hamza Bencherif, David Beresford, William Bull, George Donnelly, Jonny Gorman, Martin Gritton, Guy Madjo, Ollie Norburn, Percy Richards, Tony Waiters.