When the sides met in January 2000, the Stags had climbed to 16th, with Steve Cotterill's men lying in 13th. It was Grayson again who proved to be the difference between the teams and the Yorkshireman hit his eighth goal of the season to secure a double for Cheltenham. They went on to narrowly miss out on the play-offs, while Billy Dearden's side finished in 17th.
The clubs met on the opening day of the 2000/01 season at Whaddon Road. An own goal from Mark Blake after 16 minutes put Cheltenham ahead. The lead only lasted for five minutes and one of the best goals seen at Whaddon Road in recent years levelled things for Mansfield. Chris Greenacre tried his luck from just inside the Cheltenham half and the ball was soon hitting the back of the net. Steve Cotterill was always an admirer of Greenacre's talent and it was no surprise when he swooped to sign the striker when he was manager of Stoke.
With six minutes left, Blake atoned for his earlier error and put Mansfield ahead. It looked as though Cheltenham's opening day losing steak was to continue, but Neil Howarth poked home an equaliser to earn his side a point.
Loanee Chris Iwelumo was included in the Cheltenham line-up as they attempted to end a run of four successive defeats with a February trip to Mansfield. Clearly low on confidence, Cheltenham fell behind to an early Blake goal and an unfortunate own goal from Steve Book made it 2-0 to the home side. The 'keeper saw a shot that had hit the bar rebound of his back and into the empty goal. Iwelumo did manage a consolation debut goal, but Cheltenham's miserable run continued.
The 2001/02 season saw both Cheltenham and Mansfield in contention for promotion to Division Two. Although both eventually managed it, there was an almighty battle for the third automatic berth.
Two goals from starlet Craig Disley and a last minute Wayne Corden strike gave the Stags a thrilling 3-2 win at Whaddon Road. Julian Alsop had come off the bench and bagged a quick brace to cancel out Disley's double, but Corden broke Cheltenham hearts.
Over 8,000 fans gathered at Field Mill for the return fixture in early April. Greenacre opened the scoring for the home side after four minutes. Cheltenham skipper Mark Yates headed 25th minute leveller to throw the match wide open. Big striker Andy White was the hero for Mansfield as he scored the 77th minute winner.
The race took another twist the following Saturday as Mansfield lost 3-1 at York. Cheltenham beat Oxford 2-0 on what was the penultimate Saturday of the season. This meant that Cheltenham's destiny was in their own hands. However, a draw at Carlisle and a defeat at Champions Plymouth meant that Mansfield's 2-0 win over the Cumbrians on the final day secured the final promotion spot. Cheltenham were forced to settle for a play-off place.
Cheltenham recorded two wins over Mansfield in Division Two. Goals from Hugh McAuley and Jamie Victory earned Cheltenham a 2-0 away win.
A relegation crunch game brought a vital home win for the Robins. Goals from Martin Devaney, Marvin Brown and Damian Spencer sealed a 3-1 win. Unfortunately both sides were relegated after just one season in Division Two, but both will be hoping for another taste of the higher level in the near future.
Last season saw Cheltenham on the receiving end of a 4-0 hammering at Field Mill, but goals from Karl Henry, Damian Spencer, Paul Brayson and Kayode Odejayi gave the Robins a thrilling 4-2 win at Whaddon Road.