The unexpected departure of player manager Sid Bishop at the end of the 1965/66 season provided the opportunity for goalkeeper Dave Underwood to undertake a similar role for the season 1966/67, He had impressed  United officials during a charity match whilst being registered for Dunstable Town, and his prior League experience made him a worthy contender for the vacant Manager role. He had spent three spells at Vicarage Road for Watford, the first ending in December 1953 when he joined Liverpool.

Underwood would never forget his debut for Liverpool for all the wrong reasons. Full-back Eddie Spicer, who had been a fantastic servant for Liverpool, never played after this fateful match against Manchester United on December 19, 1953. Underwood only met his new teammates at the hotel in Manchester before the match and as Spicer recounts they were not familiar with his playing habits: "We didn't know anything about him. After about 20 minutes the ball came hard and low across the penalty box and I went for the ball expecting our goalkeeper to come out and drop on it. Instead he just took a woof at it with his boot, missed the ball and hit me. He was very upset about it afterwards and blamed himself for it." That mighty blow disintegrated Spicer's left leg and in all he had 19 fractures and he never played again. Making only infrequent appearances Underwood returned to Watford in July 1956.

 Underwood had three spells at Watford (1952-3, 1956-7 and 1960-63) and was a very popular figure at the club before moving to Fulham and then Dunstable Town and was admired by a youthful Peter High who watched him in his role as ball boy at Watford.

Underwood used his contacts at Hastings to good effect and former Watford colleagues Ken Nicholas and Tony Gregory joined United (Gregory had played in the 1958/59 Cup Final). Bobby Smith started the season under Underwood and he had played in two Cup Finals in the 1960s. It must be unusual for a non league Club to have had two former Cup finalists in a season’s squad. Former Irish international Ray Brady joined to steady the defence  and despite a shock FA Cup elimination at Horsham maintained the running in the promotion race. There were some problems along the way and in October Underwood wrote in his programme notes “The only thing I regret is the abuse I am getting from a few spectators. As soon as I can secure a good goalkeeper to take my place, it shall be done, as running two jobs as player and manager falls heavily on me.”

In the event United secured promotion to the Premier Division. Underwood had finally secured the services of goalkeeper Mick Cullen, but for the last home game against Canterbury City he needed to take up the substitutes role as an outfielder. Injury to Alan Davis meant that Underwood played the final seven minutes  on the field and  quickly earned a caution for a clumsy tackle . This proved to be his last match at United and moved on opening up the vacancy for defender Keith Rutter, as player manager, the following season.

Ricky George a former Oxford United winger who joined Hastings United the following season ( and who was a guest recently with John Motson at Hastings) said:

“Dave  was manager and goalkeeper with a face like an old-time prize fighter; a broken nose, swollen lips. He also talked with a lisp. I was always notoriously late for games and I remember one Sunday we were playing the inmates of Ford Open Prison and Dave told me the kick-off was two o'clock. At five to two on the dot I rushed in breathlessly to find an empty dressing room. About a quarter of an hour later, big Dave strolled in with the rest of the players grinning fit to burst: `Whoopth-a-daithy,' he says, `I've thuthed you out Ricky, alwayth late. Kick-off'th at free.' I loved the man, I truly did."

 In 1977 Underwood was the chairman of Barnet from the 1977/78 season to 1981/82. In his tenure at the club Barnet signed footballing great Jimmy Greaves, who later thanked Underwood for helping him in the fight to overcome his much-publicized personal difficulties.  He died in South Africa in 1989.