May began his career at Southampton's youth academy in 1998, before playing at Fulham's centre of excellence for a year. In 2000, he re-moved, this time joining Millwall's youth set-up. Ahead of the 2002–03 season, May signed his first professional contract with the club, making his debut in August 2002. He was loaned out to Brentford, and then Colchester United, during his six-year tenure at Millwall. In September 2007, May joined Scunthorpe United on a three-month loan deal, which was made permanent in January 2008. However, his time at Scunthorpe was plagued with injuries, and he was subsequently released in May 2010. May signed for Stevenage on a free transfer in October 2010, and was part of the squad that earned promotion to League One during the 2010–11 season. After struggling for first-team appearances the following season, May joined League Two side Barnet on loan. He was released by Stevenage in May 2012, and subsequently signed for Dover Athletic ahead of the 2012–13 season. After a successful season at Dover, May then joined Ebbsfleet United in June 2013.
May started his career at Southampton's youth academy in 1998, and went on to play at Fulham's centre of excellence for one season. In 2000, at the age of 16, May moved to Millwall, progressing through the youth system and onto the periphery of the first-team. In November 2001, May was an unused substitute in Millwall's 2–1 home defeat to Gillingham. He made his debut for Millwall at the start of the 2002–03 season, coming on as a 62nd-minute substitute in Millwall's 0–0 draw away at Watford on 13 August 2002. Four days later, May started his first match for Millwall, playing 68 minutes in Millwall's 1–0 away loss at Gillingham. He scored his first goal in the club's following match against Ipswich Town, scoring after four minutes to give Millwall the lead in a game that ended 1–1 – the club's website reported that "May was perfectly placed to stab home from close-range after Neil Harris worked well to carve out an opening". May featured periodically as a substitute in the opening months of the 2002–03 season, although he did not play a first-team game for three months after being substituted after 59 minutes in a 1–0 loss at Crystal Palace on 7 December 2002. He made a late substitute appearance in Millwall's 2–0 home loss against Norwich City in March 2003, before 27 March, when he joined Colchester United on loan until the end of the season. He made his Colchester debut two days after signing for the club, playing the whole match as Colchester secured a 1–0 victory over Swindon Town. May made five further appearances for Colchester, hitting the crossbar with a header in his final game against Queens Park Rangers after coming on as a late substitute. He made six appearances for Colchester, before returning to Millwall in May 2003.
May did not play for Millwall at the start of the 2003–04 season, and was consequently loaned out once more, this time to Brentford on 25 August 2003. He joined the club on an initial three-month loan deal. He made his debut in Brentford's 2–1 home win against Oldham Athletic, playing the whole match. May scored his first goal for Brentford two weeks later, on 6 September 2003, in a 3–1 loss against Plymouth Argyle, scoring the goal that briefly tied the game at 1–1. He received the first red card of his career when he was sent-off for violent conduct in a Football League Trophy match against Barnet on 14 October 2003. Four days later, he scored Brentford's fourth goal in the 87th minute in a 4–2 victory against Luton Town, turning in Jay Tabb's cross. In Brentford's next league fixture, May scored his third goal of the season, "bundling home Brentford's third" in a 4–0 win against Brighton & Hove Albion at Griffin Park. In November 2007, May's loan deal was extended until the end of the 2003–04 season. Millwall manager Dennis Wise stated "He will do very well under Brentford manager Wally Downes and will learn a lot under him. I didn't feel he was quite ready for our first-team just yet". A month later, he scored the opening goal of the game in a 2–1 home defeat against Bristol City on 26 December 2003, scoring with a header from Stephen Hunt's corner. May scored two goals in the space of a week in January 2004, scoring the equaliser in games against Oldham and Tranmere Rovers respectively. He scored his seventh goal of the 2003–04 campaign in a 2–1 loss at Swindon Town — "confidently firing home a left-footed shot from ten yards", although Brentford went on to lose their fourth consecutive match. It was May's last goal of the season, in all he scored seven goals in 43 appearances as Brentford finished the season in 17th place. He returned to his parent club in May 2004.
Ahead of the 2004–05 campaign, May re-joined Colchester United on a two-month loan deal. He impressed in a friendly match against Premier League side Charlton Athletic, scoring in a 2–2 draw, and this resulted in Phil Parkinson bringing May back to Layer Road for a second time. May started the season making four late substitute appearances as Colchester started the campaign by winning three of their four opening fixtures. He started his first game in a 4–1 home victory over Doncaster Rovers on 28 August 2004. He scored his first goal for Colchester in September 2004, scoring the club's third goal in a 3–1 away victory at Bournemouth. Ten days later, May scored again in Colchester's 2–1 victory over Premier League side West Bromwich Albion, coming on as a substitute in the 73rd minute and scoring from a "goalmouth scramble deep into extra time". In October 2004, May's loan deal was extended for a further month. Colchester manager Phil Parkinson stated — "We've extended the deal because he has done well and scored one or two vital goals for us. He is still developing but he has the potential to keep improving and he is an excellent lad to have around". After Colchester's 1–1 draw at Blackpool on 16 October 2004, May and Colchester team-mate Craig Fagan were charged by the Football Association after "a brawl broke out late in the game following an off-the-ball incident" — with May being charged with violent conduct. Two days later, it was announced that May would serve a three-match suspension, with Colchester being fined £6,000 after failing to control their players. As a result of his three-game ban, May made his last appearance for Colchester as a 74th-minute substitute in a 2–1 home defeat to Wrexham on 19 October 2004. He made 15 appearances during his three-month loan spell at Colchester, scoring twice. In December 2004, May signed for Brentford on a one month's loan deal, having previously spent the 2003–04 season with the club. After playing in the club's FA Cup draw with Hinckley United, he scored in a 2–0 win over Luton Town two days later when he "touched home Kevin O'Connor's near post cross". His loan spell was subsequently extended for a further month in January 2005. May provided assists in away victories at Luton Town and Port Vale respectively, and his loan was again extended for another month in February 2005 – with Brentford manager Martin Allen "delighted" with May's development. May returned to Millwall in March 2005, having scored one goal in 16 appearances during his loan spell at Brentford. He made eight appearances for Millwall towards the latter stages of the 2004–05 season, scoring one goal – a penalty in a 4–3 home win against Crewe Alexandra on 9 April 2005 – in a game that Millwall had thrown away a three-goal lead before May's goal proved to be the winner.
In May 2005, Millwall took up the option to extend May's contract for a further year, meaning he was contracted to the club throughout the 2005–06 season. He made his first appearance of the season in Millwall's opening match of the campaign away at Leeds United on 7 August 2005, coming on as a 79th-minute substitute for Jay Simpson in a 2–1 defeat. May made his first starting appearance of the season in a 5–0 defeat at Reading, before scoring his first goal in late August 2005, "levelling with a spectacular strike" in a 2–1 home loss against Ipswich Town. He scored again two days later, "firing a shot into the bottom corner" to restore parity in a game against Luton Town that Millwall went on to lose 2–1. May's third goal of the campaign came in a 3–2 away win at Mansfield Town in the League Cup in October 2005. His fourth goal of the season came in a 1–1 away draw with Crystal Palace, heading in Jody Morris' free-kick to give Millwall the lead. May scored three goals in three games in February 2006, the first of which came in another 1–1 stalemate with Crystal Palace, with May scoring an equaliser from eight yards in the 89th minute to salvage a point for Millwall. His other goals came in the following two games against Stoke City and Luton Town respectively. May's fine form continued when he scored in Millwall's surprise victory at promotion-chasing Watford – the BBC reported that the goal came "in injury-time, as Watford hunted for an equaliser... Ben May drilled in a low shot after a swift counter-attack". He took his 2005–06 goal tally to eleven goals when he scored twice on the final day of the season in a 4–2 defeat at Crewe Alexandra. May finished as Millwall's top goalscorer for the season with 11 goals in 44 games, although Millwall were relegated to League One as a result of finishing in 23rd place. In April 2006, May was offered a new two-year contract with the club, which he signed after speaking to new Millwall manager Nigel Spackman in May 2006 — "I spoke with the new manager briefly and I cannot wait to start working with him now".
During pre-season, ahead of the 2006–07 campaign, May injured his shoulder in training, resulting in him missing the club's pre-season tour of Iceland. Millwall manager Nigel Spackman revealed that May's injury would rule him out of the first two months of the season — "He fell over during the close season, and it looks like he is going to be out for a couple of months". He made his first appearance of the season in October 2006, coming on as a second-half substitute in Millwall's 2–0 home win against Bournemouth in the Football League Trophy, scoring Millwall's second goal with his first touch of the game. In his first start of the season, he scored after six minutes in the club's 2–1 FA Cup win against Havant & Waterlooville in a game played at Fratton Park, netting from close range after good work from Chris Hackett. Five days later, he provided the assist for Darren Byfield's goal in a 2–2 home draw with Doncaster Rovers. May scored his third goal in five appearances when he scored in Millwall's 3–1 loss at Nottingham Forest on 24 November 2006. After Millwall's 2–0 home win against Bradford City, a game in which May assisted Filipe Morais in scoring Millwall's first goal, Millwall manager Willie Donachie stated — "There's more to come from this team, especially Darren Byfield and Ben May, who are as good as anyone in this league. They're committed, honest players who want to work for each other". Three days later, on 12 December 2006, May's pacey cross resulted in Nathan Doyle putting the ball into his own net, giving Millwall a 1–0 win against Bradford City after extra-time in the FA Cup. May scored the only goal of the game in a 1–0 victory at Yeovil Town on 3 February 2007, converting Darren Byfield's cross to give Millwall the three points. However, he was substituted after 53 minutes in the same game with an ankle injury, and in March 2007, he was ruled out of first-team action for the rest of the 2006–07 season. Despite this, he made a second-half substitute appearance on the last day of the season in a 2–2 draw at Bradford City, assisting Darren Byfield's goal just after coming on. May scored four times in 19 appearances in a season disrupted by injuries.
May started the first four of Millwall's games at the start of the 2007–08 season, before scoring his first goal of the campaign in a 3–2 away loss at Swansea City in the Football League Trophy on 4 September 2007. After making a spate of substitute appearances for Millwall at the start of the campaign, May joined Championship side Scunthorpe United on a three-month loan deal. He made his debut in Scunthorpe's 1–0 win at Colchester United on 29 September 2007. May made a total of five appearances for Scunthorpe, but was recalled by Millwall in November 2007 due to a number of injuries in their squad. On his return to Millwall, May played in four games for the club, scoring one goal and setting up another in a 2–1 FA Cup home win against Walsall on 15 January 2008. It was to be May's last game for the club. During his seven years at Millwall, May scored 19 goals in 95 appearances.
In January 2008, he signed a two-and-a-half-year contract with Scunthorpe United for an undisclosed fee. A day after signing for Scunthorpe, May made his debut for the club, coming on as a substitute in the 58th minute in a 2–0 defeat against Wolverhampton Wanderers. He scored his first goal for the club in a 2–1 defeat to Ipswich Town on 22 March 2008, scoring a consolation goal in injury-time. May made a total of 21 appearances for Scunthorpe during the second half of the 2007–08 season, of which six were starting appearances, scoring one goal. May featured predominantly as a substitute during the first half of Scunthorpe's 2008–09 season, scoring his first goal of the season in a 4–0 FA Cup victory against Alfreton Town in November 2008. Two weeks later, he scored twice in Scunthorpe's 4–4 draw with Northampton Town, before scoring his fourth goal in as many games three days later in a 2–1 victory over Tranmere Rovers in the Football League Trophy. He suffered an ankle ligament injury in January 2009, ruling him out of first-team action for two months. On his return, May made four late substitute appearances, although he was not involved in Scunthorpe's successful play-off campaign as the club were promoted back to the Championship after a 3–2 victory over May's former employers, Millwall, in May 2009. May made 29 appearances during the 2008–09 season, scoring four goals.
Ahead of the club's 2009–10 campaign, May scored five second-half goals in Scunthorpe's 12–0 pre-season victory against Brigg Town. He also scored in friendlies against Jersey and Lincoln City. Despite his impressive pre-season form, he was an unused substitute in the club's first three fixtures of the 2009–10 season, before suffering an ankle injury that ruled him out for a month. Having returned to training in October 2009, May suffered another setback after injuring his other ankle – ruling him out of first-team action for six weeks. He made his first appearance of the 2009–10 season as a late substitute in a 3–1 home defeat against West Bromwich Albion on 28 December 2009. It was to be May's only appearance of the season, and he was released by Scunthorpe in May 2010. May made 51 appearances during his two and a half-year tenure at Scunthorpe, scoring five times.
In October 2010, May went on trial with League Two club Stevenage, and featured in a "behind closed doors" friendly against Dagenham & Redbridge, scoring in a 4–3 win. Shortly after, May signed for Stevenage on a permanent basis, and was assigned the number 12 shirt on his arrival. Due to May's past history in terms of injuries, he signed a contract that was largely appearance based. Stevenage manager Graham Westley said "it's fantastic to see a player putting their football before pound notes". May made his debut for Stevenage three days after signing for the club, coming on as an 80th-minute substitute in a 0–0 draw with Morecambe. May scored his first goal for Stevenage on 7 May 2011, in the club's 3–3 draw with Bury, a result that meant Stevenage reached the play-offs in their first ever Football League season. However, he was injured after he scored the goal, and was substituted immediately after for Chris Beardsley. As a result, May missed Stevenage's three play-off fixtures as the club was promoted to League One following a 1–0 victory over Torquay United. May's season was disrupted by injuries, making a total of 22 appearances for the club, of which seven were starting appearances.
In March 2012, May joined League Two side Barnet on loan until the end of the 2011–12 season. He made a scoring debut for the club, scoring from close range as Barnet came from a goal down to win 2–1 at Port Vale. May was ever-present during his time at Barnet, making eleven appearances, as the club narrowly avoided relegation on the last day of the season. During his two-months with Barnet, he scored four times. He was released by Stevenage in May 2012.
Ahead of the 2012–13 season, May went on trial with League Two club Gillingham, training with the club for a number of weeks and playing in several pre-season friendlies. However, no move materialised, and May signed for Conference South side Dover Athletic on a free transfer on 8 August 2012. May made his competitive debut for Dover in a 2–2 away draw against Sutton United on 21 August 2012, coming on as an 86th-minute substitute. He made his first start four days later as Dover defeated AFC Hornchurch 1–0 at Hornchurch Stadium, before scoring his first goal for the club in a 3–1 away win at Eastleigh on 1 September. May went on to score in seven consecutive games running from September to November, five of which in the league and a further two in the FA Cup, subsequently taking his goal tally for the season to eight. Goals in convincing victories over Weston-super-Mare and Truro City took May's goal count into double figures. He ended the year with a run of five goals in three matches, scoring braces in wins against Eastleigh and Hayes & Yeading United, as well as scoring a late consolation strike in a 2–1 defeat to Tonbridge Angels on 26 December 2012. It took May a month to get off the mark at the start of the new year, controlling the ball and scoring on the turn in a 3–2 win over Welling United at the Crabble Athletic Ground on 9 February 2013. He scored four times in March 2013, subsequently taking his tally for the season to over 20 goals – the first time May had reached this milestone in his career. He scored two further times during the regular season, in away victories against Chelmsford City and Staines Town. Dover finished the season in third place, meaning they would play fourth placed Eastleigh in the two legged play-off semi-finals. May scored a dipping volley as Dover took a 3–1 lead in the first leg, controlling the ball on his chest with his back to goal, turning and hitting the ball from 25-yards past Ross Flitney in the Eastleigh goal. Dover progressed to the final, but lost 3–2 to Salisbury City after extra-time, with May playing in all three play-off matches. During his one season at Dover, May finished the season as the club's top goalscorer, scoring 24 times in 45 matches.
In June 2013, May signed for Conference South side Ebbsfleet United. On joining Ebbsfleet, May said — "It's all exciting stuff; Steve Brown showed an interest in signing me as soon as he knew he would be manager of Ebbsfleet. I’m currently enjoying a nice little break from football but I’m itching to lace my boots up and get back on the pitch". He eventually left the club in January 2015.
Following his departure from Ebbsfleet, May signed for league rivals Bromley, the team for which his brother, Jay, had played for the previous season. Following an injury hit spell at the club as a player, May assumed the role of first team fitness coach, following the departure of Jon Rayner.
May was born in Gravesend, Kent. May states that his favourite footballers when growing up were Alan Shearer and Ian Wright as he believed they were "great goalscorers and always entertaining". He enjoys watching the television sitcom Only Fools and Horses. May is good friends with England international footballer Glen Johnson, as well as Sheffield Wednesday striker Gary Hooper. He attended Leigh CTC School in Dartford alongside Johnson.
In January 2007, it was reported that May and England defender Glen Johnson were caught at a B&Q store in Dartford, Kent, attempting to steal bathroom fittings. They both received £80 fines. Johnson described the incident as "comical" because it was a misunderstanding — "Ben was doing up his bathroom so we went to B&Q and found one of those sets where you get everything in one box. But he wanted a seat with a slow-close lid, so we took out the seat and put in another one. What we didn't know was that the new seat was £2.35 more expensive. We went through the till, paid for it and then the security guard stopped us and said he had been watching on CCTV. We just burst out laughing. Where's Jeremy Beadle then? But he said, 'No, this is serious, the police are on their way.' The police turned up and they were laughing. I said to the security guard, 'Can we not just pay the £2.35?'" He said, 'No, this is a serious offence.' So the police gave us two options: go to court and fight it out, or pay an on-the-spot fine. We couldn't be bothered going to court so we paid the fine but doing that made us look guilty".
His older brother, Jay (engaged to Gina Riley) and younger cousin, Alfie are also footballers. Alfie currently plays for Erith & Belvedere, while Jay is with Maidstone United.Scunthorpe United
League One play-offs (1): 2008–09
League Two play-offs (1): 2010–11
As of 26 March 2016