We continue our look back at the Silkmen stars of yesteryear by featuring by combative defender who captained the side during our millennium season.
Gregor was born in the mid-1970's in Sutton Coldfield. The son of former Scottish international and Arsenal manager Bruce, Gregor was perhaps destined to follow in his Dad's footsteps.
He did exactly that, joining Luton Town as an apprentice just as his father had done twenty years earlier. Turning professional with The Hatters in 1993, he unfortunately failed to make a First Team appearance and spent some time on loan with Barnet before leaving Kenilworth Road in search of more game-time.
Having made his league debut as an eighteen year old at Barnet, Gregor then signed for Peterborough United in 1995. Although regular starts were slightly sporadic, he impressed enough in his nineteen games for The Posh to catch the eye of scouts at Hull City. Signing for The Tigers in the summer of 1996, it was at Boothferry Park that Gregor really made his mark on the game.
Hull experienced some turbulent times in the mid-1990's, following years of financial difficulties. They were relegated to the old Third Division in 1996 and Gregor was one of the players to join The Tigers in a bid to steady the ship. Manager Terry Dolan made the twenty-two year old club captain in 1997 - a post that he proudly held until his departure in 1999 after making over one hundred appearances for the club.
Over in Macclesfield, The Silkmen had experienced a very different few years to The Tigers. Two promotions in as many seasons had taken the club into the Second Division (now League One), albeit for a single season. It was following Macc's relegation to Division Three in 1999 that Gregor crossed The Pennines to join the club.
Gregor had helped mastermind “The Great Escape” as captain at Hull City, staving off relegation from Division Three when it looked almost inevitable. With Macclesfield aiming to return to the third tier at the first time of asking, manager Sammy McIlroy handed the captain's armband to Gregor at the start of the 1999/00 season.
Although relieved of this duty a few months later after McIlroy felt it may be too much for him, Gregor impressed on the pitch with his commitment, enthusiasm and professionalism. He was an almost ever-present that season, with forty-seven appearances in all competitions and five goals. One of the these came against former club Hull, in the form of a first half penalty.
Injury affected Gregor’s chances in the season that followed and as such, his appearances for the team were limited. Looking for new opportunities, he moved on in March 2001 to join Shrewsbury Town. Eighteen months at Gay Meadow followed, during which the club narrowly missed out on the play-offs before he moved back to Cheshire as he joined Northwich Victoria.
The next few seasons were spent between Shrewsbury and Northwich, with a second spell at each. Gregor then rounded off his eleven year playing career at Leigh RMI before making the move into management.
On leaving Leigh, Gregor went abroad and was appointed Manager of Danish club Koge BK. As the youngest manager in Denmark at twenty-eight years of age, he spent two years with Koge before returning to England in 2006.
Gregor became the manager of Manchester City's Under 17 squad and subsequently took over the Reserve Team.
A successful spell as Academy Manager at Coventry followed, before it was announced that Gregor had joined Wigan Athletic in December 2013 in a similar role as he became responsible for all the club's young players from nine to twenty-one years old.
Gregor has perhaps found his niche as a coach, but Silkmen fans will certainly remember his short time captaining the squad as a player in the late 1990's.