Whitby's most prestigious honour is arguably the FA Vase, which they won in 1996–97 after defeating North Ferriby United at Wembley Stadium.

The club's colours are somewhat distinct in English football and are intentionally similar to Italian side Sampdoria[1] wearing a blue shirt with a touch of white, black and red.

[3] The name was changed in late 1882 to Whitby Football Club and continued to play friendly games as well as competing in the Scarborough & East Riding County Cup.

A 0–0 draw against Hull City in the first round proper of the FA Cup, was played at Scarborough on police advice, in a remarkable replay at Boothferry Park, Whitby came from behind to take a 4–3 lead which was held until the dying moments of the game.

The following season, 1997–98, saw continued success at the Turnbull Ground when the club won the Northern Premier League First Division Championship by a margin of 7 points at their first attempt as well as beating York City 3–0 in the final of the North Riding Senior Cup to become holders for a fifth time.

In the 1999–2000 season the Seasiders finished 12th in the Northern Premier League and were beaten finalists in the President's Cup, losing over two legs to Trafford after a penalty shootout.

The 2001–02 season saw Whitby finish in a disappointing 15th in the league, but got to the FA Cup 1st round for the 7th time, only to lose out to Plymouth Argyle after a replay, 3–2.

Whitby also managed to finish in the play-off zone for the new Conference North but went out on penalties to Radcliffe Borough, a team they had beaten 5–0, 6–2 and 1–0 in the regular season.

The former Blues stalwart turned the side around as they equalled a club record 19 games without defeat and in the process made the Northern Premier League promotion play-offs.

Senior player Phil Brumwell took temporary command of first team affairs, helped out by former Spennymoor and Tow Law stalwart Graeme Clark.

However, ground issues with Cammell Laird, meant Whitby avoided a first-ever relegation in their history, at the expense of the Merseyside club.

Clark resigned in the meantime, and the iconic Harry Dunn, sacked from Blyth Spartans despite taking them to the FA Cup third round and earning the Northumberland club £400,000 months earlier, began a second spell as Whitby manager.

Dunn, who brought a spell of unprecedented success to Whitby, returned to the club on 14 May 2009, two days after Graeme Clark's resignation and steered Town to a respectable 14th place.

This despite looking good for a top half position before an unprecedented number of injuries and suspensions – including three sendings off in one match against Nantwich Town on 2 April 2010 – led to six straight defeats to end the campaign.

Despite overseeing an unbeaten three match spell, Scaife departed by mutual consent, after a number of volunteers resented him for taking his full contract entitlement, when he was dismissed as manager in 1995.

Williams quickly moved to bring back players who left during Cassidy's reign- popular local lad Ashley Lyth and two-time top goalscorer from midfield, Jimmy Beadle- plus he also brought in experienced strikers Andy Appleby and Jamie Clarke to bolster a struggling forward line, alongside ex-Bolton winger Jeff Smith.

Nathan Haslam On 2 April 2019 the contracts of Chris Hardy and Player/Assistant Manager Lee Bullock were extended by two years, until the end of the 2020–21 season.