Friday night draw (1999/2000)
Whitby manager Harry Dunn gave debuts to three players in this Friday night fixture against Gainsborough, handing a debut to ex-Celtic and Grimsby midfielder Jim Dobbin and two players on loan from Bury, midfielder Paul Donnelly and forward Gary Messer. The game was switched to Friday night to avoid a clash with the England vs Scotland Euro 2000 qualifying tie played on the Saturday afternoon/ It was Messer who had the first chance of the game, shooting just wide after Dobbin had set him free, then on fifteen minutes a David Logan free kick was headed towards goal by Lawrie Pearson but it was hooked away to safety. Trinity then had a chance on 22 minutes but Whitby keeper Stuart Dawson made a great double save to foil Allison before Whitby took the lead in the 27th minute when the on loan Messer seized on a loose ball to hammer home past Curry from 18-yards. The home side fought back and equalised after 34 minutes when Drayton crossed for Reed to nip in and head home past a static away defence for 1-1. The second half saw Whitby withstand the home sides' attempts to get a winner with centre backs David Goodchild and Ben Dixon in fine form and Whitby had a chance to claim all three points with 15 minutes to go when Craig Perry freed Paul Stout but his low 18-yard drive was superbly saved by Curry and both sides had to settle for a point.

The first win (2000/01)
Whitby recorded their first victory at Gainsborough’s Northolme ground thanks to two goals in two second half minutes to see Harry Dunn’s side come back with the points and end the home side’s unbeaten home run. Gainsborough went ahead after eleven minutes when Lee Ellington’s low cross was fired home past Whitby goalkeeper David Campbell by Gavin Bassinder from 6 yards out. At the other end Mark Taylor was unlucky not to equalise for Town when he saw his shot cleared of the line by Brown, but Whitby found an equaliser on 38 minutes. Craig Skelton and Anthony March combined to set up Lee Ludlow who turned his marker and he fired past Steve Curry and inside his near post for 1-1. Whitby gained the lead on 69 minutes when David Logan sent a free kick into the Gainsborough area and Taylor was there to glance home a header, and just a minute later Whitby doubled their lead. Michael Pitts got free down the right wing and his cross was met by Graham Robinson who powered a header past Curry to give Whitby the victory. With six minutes remaining Whitby had Kevin Graham sent off following two yellow cards.

Late drama (2002/03)
A Mark Swales goal a minute before full time gave Whitby all three points in Lincolnshire. The home side started the brightest and had the first chance of the game after six minutes with Grant getting to the by-line and pulling the ball back for Camm who shot straight at David Campbell from eight yards out. Camm then got on the end of a Lee Ellington cross, but with the goal at his mercy he put his shot wide. Whitby’s first effort on goal came in the 18th minute when from a Daniel Lowe cross Lee Ure put his header wide before in the 31st minute good work from Aron Wilford saw him beat a defender and get to the by-line before getting a cross in that Ure fired into the side netting. Both sides had chances early in the second half with Trinity’s Grant seeing his shot strike Campbell’s cross-bar before Wilford’s shot at the other end was headed off the goal line by Timons. Wilford then brought a good save from Trinity keeper Pettinger who tipped his free kick over the bar before Campbell made a good save from Ellington. With seven minutes left Swales released Alex Gildea who got clear but Pettinger made a tremendous save to keep the score at 0-0 but with a minute left a short corner was played to Swales who from 25-yards out fired the ball into the top far corner of the Gainsborough net to give Whitby the victory.

Gainsborough's fight back (2003/04)
Harry Dunn’s Whitby side had to settle for a point after Gainsborough fought back from 2-0 down at the break to earn a point and keep their unbeaten home record. The home side had the first real chance of the game when a free-kick into the box was headed just wide by Luke Stanton before Anthony Ormerod tried his luck from 25-yards out, shooting well wide. Whitby goalkeeper David Campbell then made a great save to keep out Lee Ellington’s 18-yard effort after 13 minutes. Four minutes later Whitby took the lead when an Ormerod corner from the left saw Tony Hall and Brian Linighan get in headers before the ball fell to the feet of Linighan to soot home from eight yards out. Whitby then shocked their hosts by doubling their lead on 28 minutes. Ormerod fed Andy Appleby down the middle and the on loan Hartlepool United youngster outpaced the defence but keeper Paul Norton made a superb save only for the ball to rebound to Appleby who fire home into the roof of the net. Whitby started the second half on top with Ormerod and Graeme Williams going close before the home side pulled a goal back on 59 minutes. Ellington turned and crossed for Richard Byrne to score at the far post with Whitby appealing for offside. Trinity then replaced Byrne with Scott Stancill in the 71st minute and he instantly made an impact on the game. Trying to get to a Burley cross inside the visitors area he was brought down by Campbell and the referee awarded Trinity a penalty. Ellington stepped up to beat Campbell from the spot and make it 2-2. Both sides had chances before the end of the game with Campbell doing well to keep out a Stanton free kick and Appleby seeing his shot tipped wide as the sides settled for a point.