1999 / 2000 - Goodbye Sammy

To enhance the playing surface, new drains and a new surface was laid before the season started. Key departures included Niel Sorvel, Steve Payne, Pedro Matias and Efe Sodje.New recruits included Gregor Rioch and striker Richie Barker.

Early season form was mixed with side in a mid-table position although they dipped to 21^st place at one stage.Richie Barker made an immediate impact scoring on his debut and regularly afterwards and went on to complete the season as the team's top-scorer.

November saw the Silkmen scoring five goals for the first time since promotion to the Football League in the 5-2 defeat of Mansfield Town and Darren Tinson became the first of the former Conference players to reach 100 League appearances.

In Cup competitions there was little joy for the Silkmen as they were knocked out in the second round of the Auto Windsreens Trophy by Rochdale who won on the 'Golden' goal rule.There was no repeat of the previous year's success against Stoke City in the Worthington Cup when the Potters won 4-1 on aggregate and Hull City disposed of the Silkmen in the FA Cup following a first round replay. However, the Cheshire Senior Cup was won for a record 20^th time with a 2-1 victory over arch rivals Altrincham.

December saw a rise in the team's fortunes completing the month in 6^th position.Along the way they had to play in Shrewsbury's away strip when the referee deemed both strips were too alike and Chris Priest's 90^th minute goal in the 2-1 win over Carlisle was officially recognised as the last Football League goal to be scored in the millennium. The club received a loan of £60,000 from the PFA to cover players' wages but with the stipulation that no new signings would be permitted until the loan had been repaid.

In January Sammy McIlroy left the club on his appointment as manager of the Northern Ireland team, thereby ending the most successful period in the club's history. During his time at Macclesfield Sammy had won every non-League competition available, the Conference Championship on two occasions and promotion to the third tier of English football.

Peter Davenport, Sammy's assistant, was appointed manager and he made an excellent start with a 2-1 victory over Darlington. There were good wins against Barnet (2-0) and Hartlepool (4-1) but in March top-scorer Richie Barker was injured but his absence gave young striker Damien Whitehead his opportunity. Damien did not disappoint with two goals in the 4-2 victory over Shrewsbury Town but it was his performance in the 4-1 victory over Plymouth Argyll which saw his best performance when he scored two goals and was provider for the other two goals.

Results for the remaining matches were mixed, however, there were two interesting events. Mike Bamber must have made one of, if not the shortest ever, league debut for Macclesfield when he came on from the substitutes' bench at the end of the penultimate match of the season for a mere 21 seconds. In the last match of the season at Halifax, Town Darren Tinson scored his first League goal in 127 league appearances to win the match for the Silkmen. Their first season back in the fourth tier of English Football saw the team finish in a mid-table position.

2000 / 2001 - A brand new stand

Three experienced players were signed, former Manchester United player Simon Davies, striker Lee Glover who had made appearances for Nottingham Forest and former West Ham United midfielder Kevin Keen. The season started slowly but there was an exciting 4-4 draw at Mansfield with Damien Whitehead scoring a late equaliser, but the highlight was the first ever live broadcast from the Moss Rose by Sky Sports against Darlington which ended in a 1-1 draw.

October was a successful month recording three wins, a doubling of league points from 11 to 22 and a move up the table to 10^th position.However, there was a complete contrast in November with no victories and a return to a mid-table position.

In Cup competitions there was excitement with an aggregate win of 3-2 against Bolton Wanderers including a 3-1 win at the Reebok Stadium in the first round of the Worthington Cup. Middlesborough won the second round 5-2 on aggregate.Oxford were victors in the first round of the FA Cup but their supporters unhooked the net on two occasions, the second just before Lee Glover's unsuccessfulpenalty. Having been awarded a bye in the first round of the LDV Vans Trophy, A 4-2 defeat at the hands of Chesterfield saw the Silkmen bow out in the second round..

December was a disappointing month for results and having lost the Boxing Day match 1-0 against York City and the side in 15^th position the directors asked Peter Davenport to work alongside Director of Football Gil Prescott. Davenport could not accept this request and left the club with GilPrescott then appointed manager.

Richie Barker had been placed on the transfer list in December and with identical bids from Rochdale and Rotherham, Richie opted to move to Rotherham only seven miles from his home, a move which netted the club £100,000.

January proved a difficult month but results were more favourable in February including a 3-1 victory against Plymouth when Chris Priest scored two goals, a 2-1 victory against Shrewsbury Two with Damien Whitehead scoring both goals and a John Askey 90^th minute goal to secure a 2-1 victory against Lincoln City. Results for the remainder of the season ensured that the Silkmen finished in a mid-table position.

The newly built Alfred McAlpine stand was used for the first time on Sunday 11 March when Sammy McIlroy performed the formal opening. This was one of three matches which had been moved from the regular Saturday kick-off to a Sunday in an attempt to increase attendances. The final match of the season saw the East Cheshire Pipe Band provide pre-match entertainment and Tom Pendry MP present a cheque for £1.95M from the Football Trust towards the cost of the stand and ground improvements.