"We're on our way" (2017)
Chris Hardy’s Whitby side made it through to the semi-finals of the North Riding Senior Cup after overcoming Conference Premier side York City.
They opened the game brightly and took the lead after five minute when Callum Martin got down the wing and his pin-point cross was met by the unmarked Steven Snaith to head past Luke Simpson at the near post.

York hit back and Daniel Nti had a shot deflected wide and from the resulting corner Whitby keeper Shane Bland pulled off a great reaction save to keep out Vadaine Oliver’s close-range header before future Blue Matthew Dixon saw his cross headed just over by Nti.

On 34 minutes Bland pulled off another great save, this time to push away Callum Rzonca’s long-range effort that was heading towards the top corner of his net.

Five minutes into the second half Whitby doubled their lead when substitute Luke Bythway headed home past Simpson from a Martin corner, but straight from the restart the visitors pulled a goal back when Oliver rose to head home following a corner.

Danny Galbraith then fired a free-kick straight at Bland before Whitby regained their two goal advantage.

David Carson started and finished the move with 25 minutes to go when he set Dale Hopson away down the wing. Hopson pulled the ball back for Carson to fire past the advancing Simpson into the top corner of the net for 3-1.

Hopson had a chance to make it four with eight minutes to play after a mistake from Luke Woodland but he fired his effort high and wide.

Setting it up for derby day (2003)
Whitby progressed through to the North Riding Senior Cup semi-finals and set up a tie against local rivals Scarborough after overcoming the Minstermen who had nine players with Football League experience in their side.

The first chance fell to Whitby on six minutes when Aron Wilford headed down for Graham Robinson to volley over the bar from close range, before ex-Whitby goalkeeper John Collinson did well to keep out Lee Ure’s angled drive.

Whitby went ahead on 25 minutes when Ure set up Tom Reid 20 yards from goal and he fired a low drive past Collinson and into the bottom corner of the net.

Alex Mathie then got free four minutes before half time but just as he was about to shoot, Michael Laws got back to make a saving tackle and clear the danger.

Ten minutes into the second half Whitby doubled their lead when Wilford got down the byline and crossed for Robinson to tap home and they made the tie safe with 13 minutes to go.

A scramble inside the York penalty area involving Stefan Zoll and Alex Gildea, as well as two opposition defenders, saw the ball fall to Wilford who scrambled the ball home for his 20th goal of the season.

One to forget (1995)
York City manager Alan Little brought his full first team squad to the Turnbull Ground for this friendly fixture, only the second time the sides had met in such a fixture, the first friendly meeting being at the start of the 1975/76 season with Whitby coming out on top with a 2-0 victory. This time though, Little’s men thrashed a depleted Whitby side, including ace striker Paul Pitman 6-0. Whitby manager Bob Scaife gave new signings Ian Williams and Steve Richie a run out and also included the returning Trevor Smith and David Logan in the starting line up. York included Bobby’s son, ex-Whitby midfielder Nicky Scaife, in their side. It was Paul Barnes who stole the show though scoring four second half goals with Scott Oxley and Nicky Peverill also on the score sheet. Whitby goalkeeper Matthew Coddington did well to keep the score down in the second half.

A memorable night at Bootham Crescent (1990)
Eddie Gray’s Whitby side produced a great performance to beat York City’s reserve side at Bootham Crescent in the North Riding Senior Cup.

With just five minutes played Whitby had a chance to take the lead when Eric Warbuton’s cross was headed down by Paul Sharkey to Richie Gowan whose 15-yard effort was deflected wide, and from Paul Pitman’s resulting corner Sharkey’s near post header was well saved at the foot of the post by York goalkeeper Dean Kiely, on loan from Coventry City.

Kiely then did well to save from Pitman before Whitby opened the scoring with
seven minutes to go until half time when Whitby keeper Graham Shaw sent Sharkey away down the field and he beat a defender before crossing for Pitman to fire the ball high into the corner of Kiely’s net.

Nine minutes into the second half Whitby doubled their lead when Steve French hammered the ball home past the diving Kiely from the edge of the box following a Pitman corner.

York fought back and got back into the game twelve minutes later when a free-kick from Ricky Greenough was headed back out to Geoff Thompson who looped his shot over Shaw and into the net for 2-1.

Whitby held out for the final 24 minutes to claim a great victory.

Routinely into the final (1968)
This North Riding Senior Cup game kicked off in gale force conditions, with Whitby winning the toss and so had the wind behind them in the first half and it worked to their advantage when they raced into a 4-0 lead with only 23 minutes of the game played. After just two minutes Bobby Veart fired just wide and Keith Carter brought a good save from York’s keeper Harry Fallon. Hinch then fired over at the other end before Carter gave Whitby the lead after twelve minutes, turning to shoot low past Fallon and into the corner of the net. Four minutes later Billy Theaker doubled Whitby’s lead when he scored a great goal, hammering home from 20 yards out. Three minutes later Veart was brought down inside the area and a penalty was awarded, with Veart stepping up to beat Fallon from the spot. Right-back Eddie Myers then made it 4-0 with an even better goal, bringing the ball out of defence down the right he beating the entire City defence before unleashing a tremendous shot from 30 yards that Fallon was unable to reach. Two minutes into the second half and with the wind now behind City, Stuart Alderson saw his effort rattle the Whitby bar before Theaker cleared the danger. Whitby’s defence held firm and with eleven minutes to play Tony Dobson made it 5-0 when he headed home a cross into the far corner of the City net to put Whitby through to the final which they won after beating Middlesbrough Reserves 2-1 at the Turnbull Ground.