Ahead of Crawley Town's visit to the Moss Rose on Saturday, we’ve been digging through the history books to find out who has turned out for both teams over the years...
Winning the Conference Premier with The Reds in 2010/11, he then spent some time out loan with Fleetwood, Morecambe and Grimsby before parting ways with Crawley in 2013.
Richard failed to replicate the success he experienced at York and spent time with Gateshead, Southport, Aldershot and Stockport before heading back to York in 2016.
It was during this second spell with The Minstermen that he came to Macc on loan.
Making only four appearances for The Silkmen, three of which were from the bench, Richard headed back to his parent club in January 2017 before being released shortly after.
Richard is currently playing for Ilkeston Town.
A youth player with both Manchester City and Accrington Stanley, Lewis had success with both Altrincham and Aldershot before joining Crawley on loan in 2009. He made only four appearances for The Reds before returning to Aldershot two months later.
Lewis was released by The Shots in 2010 and joined the Silkmen straight after. Making just over fifty appearances for Macclesfield, he netted five goals which included three penalties.
Released in the summer of 2012 at the end of his contract, he has since had short spells with a number of North West non-league sides.
Lewis re-signed for Macclesfield in August 2013 but made only two further appearances before being released in the September.
Irish defender Mark started his senior career with Bolton Wanderers, who paid £1 million for him on summer transfer deadline day in 2009. First Team opportunities failed to materialise and he went out on loan to St Johnstone before joining Macclesfield in 2012, another loan move.
With The Silkmen for a month, he made seven appearances in blue before heading back to Bolton who released him at the end of the season.
Mark moved to Crawley in July 2012, looking for First Team football. A strong season followed and regular games came thick and fast, with thirty-five appearances and two goals in his first season with The Reds.
Links with Championship clubs followed but Mark struggled to replicate his first season success with Crawley and was released in the summer of 2014 along with ten other players.
Mark spent two years at Kilmarnock before making the return to Crawley in 2016 - he has been a regular on the team sheet ever since.
Signing for Derby County as a fourteen year old, Pablo remained with The Rams until 2006 before joining Rotherham United. He was loaned out to Crawley at the start of the following season to regain his fitness after the summer break.
Making only fourteen appearances before returning to Rotherham, Pablo obviously impressed at Crawley as they snapped him up in 2010 when he was released by The Millers.
Pablo had two successful years at Broadfield Stadium which included the captains armband, a Man of the Match appearance against Manchester United in the FA Cup 5th round and a Conference winners medal.
Released by Crawley in May 2012, Mills fielded interest from French club Boulogne and joined The Silkmen in August. In and out of the side due to stiff competition in defence, he made his debut as a central midfielder as cover for Kieran Murtagh.
Taking over captaincy duties towards the end of the 2012/13 season, Pablo’s improved performances lead to a more regular spot in the starting line-up. Released in 2013 he re-joined Rotherham before moving to Bury, Brackley Town and Mickleover Sports.
Yorkshireman Emile first came to Macclesfield in 2009 on loan from Nottingham Forest. He impressed in his seventeen appearances and made the move permanent during the following May.
Making his debut on the first day of the new season, it took until 29th September for Emile to find the net, which he did in the 1-1 draw against Burton Albion.
Early on in the 2011/12 season Emile found his goalscoring form, scoring four times in seven games which unsurprisingly attracted attention from other clubs. Macclesfield failed to hold on to the striker and he left for Peterborough United in August 2011.
Following mixed fortunes at Peterborough, Emile joined Crawley Town in August 2013 on a two year contract.
Keen to impress manager (and another ex-Silkmen) Richie Barker, he scored his first goal for the club two weeks after his debut, but struggled to establish a place as a regular goalscorer, admitting to the local paper that he had “fallen out of love with football” in November 2013. He left Crawley in the following January transfer window.
Emile is still playing football, most recently with Goole AFC in the Northern Counties East League Premier Division.
Honourable mentions: Tyrone Barnett, Mitch Hancox, Guy Madjo, Isaiah Rankin.