Season 1999-2000 Cheltenham Town approached their first season in the Football League with a mixture of excitement and trepidation. After storming through the Conference in two seasons of unbridled success the Robins set sail upon a new adventure, their supporters still wide eyed at the glorious unexpectedness of it all.

New arrivals for the season included Antony Griffin, a £25,000 buy from AFC Bournemouth and goalkeeper Shane Higgs, who was recruited from Worcester City for £10,000. Striker Hugh McAuley arrived from Leek Town and wide player Martin Devaney from Coventry City. Other than those fresh faces manager Steve Cotterill kept faith with the core players from the squads who had served him so well in the Dr Martens League and Conference days.

The season began with a fanfare but fell flat pretty quickly as Rochdale handed out an opening day 2-0 defeat at Whaddon Road. Better was to follow at Mansfield a week later when Neil Grayson elevated his club legend status yet further by heading in the club's first Football League goal to capture a 1-0 win.

The succeeding weeks offered up a mixed bag of results as the team maintained its reputation as a hard-grafting outfit yet goals seemed particularly hard to come by. A number of forward combinations were tried and players such as Mark Jones, Chris Freestone and Jason Brissett arrived on loan. The latter produced one of the more comical moments of the season when, having thought he head the referee's whistle during a match at Rochdale, he caught the ball inside his own penalty area. The referee pointed straight to the spot but thankfully goalkeeper Steve Book was equal to the penalty kick and a point was preserved.

Among the highlights of the first half of the season were a 2-0 league win over Plymouth - featuring a colossal long-range strike from the irrepressible Grayson - and a 2-1 victory in the home leg of the League Cup first round against Norwich City.
Goals may have been hard to come by in the opening weeks but as the new Millennium dawned the Robins began to hit upon a formula that took them to the verge of the play-offs.

As their confidence and belief grew it became apparent that many of the players who had served the club in the Conference were more than equal to the task of Division Three football. Neil Howarth, Mark Freeman, Chris Banks and Jamie Victory formed a well-drilled back line with Michael Duff pushed forward to the right-hand side of midfield. His physical presence provided an ideal contrast to the delicate touch and slide-rule passing of Russell Milton on the left. With the hard running and ball-winning abilities of Lee Howells and Mark Yates in the middle the team had developed a useful blend of different players in midfield. Up front, Grayson continued to terrorise defenders with Devaney a revalation alongside him scoring important goals in the away wins at Exeter and Lincoln.

The final Saturday of the season arrived with Cheltenham needing to win at Southend and hope that Hartlepool United failed to get a result at Hull City. 1,500 fans travelled to the Essex seaside on a sunny afternoon but were to go home disappointed as the Shrimpers hit back against an early Lee Howells goal to win 2-1.

Despite this setback the season had been an immensely enjoyable debut. Fears that the club may have taken a step too far were dispelled and the fans were left with a sense of anticipation that yet more glory could be achieved.

Player of the Year: Russell Milton

Top goalscorer(s): (11) Neil Grayson & Russell Milton

Most Apearances (all comps): (53) Steve Book, Jamie Victory & Mark Yates

Average Lge Attendance: 4,146 

Nationwide Division 3: 8th - 70pts 

League Cup: R1 - Norwich City

FA Cup: R1 - Gillingham (after replay)

LDV Vans Trophy: R2 - Bristol City