Boylan began his career with West Ham United in 1995, and progressed through the club's youth academy.

Ahead of the 2001–02 season, Boylan joined Canvey Island, where he played 210 games and scored 176 goals for the club during a five-year spell.

He joined Stevenage for an undisclosed fee in June 2008, scoring in the 2009 FA Trophy Final victory against York City at Wembley Stadium in May 2009.

Midway through the 2012–13 season, Boylan signed for divisional rivals Maldon & Tiptree, which would be his last club before retiring from playing.

[3] Boylan began his career with West Ham United in 1996,[4] playing regularly in the club's youth team, as well as in the FA Youth Cup Final defeat at the end of the 1995–96 season, starting alongside Rio Ferdinand and Frank Lampard.

[6] After a loan spell with Kingstonian during the 1998–99 season, he joined Trelleborg in Sweden on a permanent basis in 1999, playing two games for the club and scoring one goal.

[7] Boylan made his debut for Exeter in the club's 1–0 defeat to Halifax Town, coming on as a substitute in the 69th minute.

[7] Boylan was without a club in the opening months of the 2000–01 season, before he joined Hayes in November 2000, making his debut in a 1–0 home defeat to Telford United.

[12] Despiting playing regularly, Boylan left Hayes in February 2001, and signed for another Conference National club in the form of Stevenage Borough two months later.

[22] During the 2003–04 season, Boylan set a club and league record when he scored in 11 consecutive games, spanning from December 2003 to February 2004.

[23] During the 11 games, Boylan scored 21 times, which included consecutive hat-tricks against Bishop's Stortford and Billericay Town, and braces against Ford Utd, Maidenhead United, Northwood, and Hayes.

[34] After scoring Canvey's second goal in a 4–1 away victory against Stevenage at Broadhall Way, Boylan was stretchered off after 27 minutes having suffered a fractured ankle.

[37] Boylan scored 16 goals in 31 games as Canvey avoided relegation to remain in the highest tier of non-league football.

[57] Boylan started in the club's 1–0 defeat to Exeter City in the play-off final at Wembley Stadium on 15 May 2008, playing the first 69 minutes of the match before he was substituted.

[60] Boylan signed for fellow Conference Premier club Stevenage Borough for an undisclosed fee on 7 June 2008.

[60] He made his debut for the Hertfordshire club as a substitute in a 5–0 defeat against Wrexham at the Racecourse Ground on 9 August 2008,[62] and scored his first goal for Stevenage in the 4–1 victory over Burton Albion on 6 September 2008.

[63] A brace against Kidderminster Harriers on 21 April 2009 ensured Boylan ended the season with ten league goals.

[66][67][68] This included scoring the second goal in Stevenage's 2–0 win against York City in the Final at Wembley Stadium on 9 May 2009, latching onto a through ball before hitting a "looping shot" over the goalkeeper to seal the victory in injury-time.

[73] After an unsuccessful trial at Southend United,[74] Boylan signed for Conference South club Chelmsford City on a free transfer on 5 March 2011.

[81] Boylan opted to stay at Thurrock for the 2011–12 campaign, scoring on the first day of the season in a 1–1 draw away at Salisbury City on 13 August 2011.

[84] Boylan joined Isthmian League Division One North club AFC Sudbury on 27 July 2012, taking on dual responsibilities as a player-coach.

[90][91] Boylan continued to play regularly for Maldon & Tiptree for the remainder of the 2012–13 season, and scored three times in their play-off campaign as they lost 4–1 on penalties to Thamesmead Town in the final.