Throughout his career, Bojinov has played for eighteen different clubs during his various spells in Italy, as well as in England, Portugal, Bulgaria, Serbia, Croatia, China and Switzerland.

[3] Bojinov was discovered at the age of 14 by Lecce sports director Pantaleo Corvino while playing for Pietà Hotspurs, and signed for just 30,000,000 ITL (around €15,000).

On 3 August 2007, it was reported that Bojinov had completed his move to English Premier League club Manchester City, signing a four-year contract in an undisclosed fee deal.

[7][8] On 11 August 2007, he made his debut for the club in a 2–0 away win against West Ham United at the Boleyn Ground, entering as a substitute for Rolando Bianchi in the 60th minute in league play.

On 11 February 2008, Bojinov played in a Manchester City reserve game, where he came on as a substitute and scored a header from a cross by Émile Mpenza.

[11] On 17 August 2008, Bojinov was ruled out for six months after suffering an Achilles injury as he was running on to the pitch to warm up against Aston Villa.

[12] In mid-February 2009, Manchester City manager Mark Hughes declared that Bojinov was going to play a practice match "behind closed doors", as he was nearing his return to first-team football.

[13] Bojinov made his first start since 2007 in a 1–0 home win over Sunderland on 22 March 2009, but was substituted in the 65th minute for the return of injured Craig Bellamy.

On 6 July 2011, Portuguese side Sporting CP signed Bojinov on a five-year contract, paying €2.6million for 80% of his registration rights, which could have risen to €3.5 million depending on his performances.

He made his first-team debut on 25 August against Danish side Nordsjælland in a UEFA Europa League play-off tie.

[25] On 20 January 2012, Sporting declared Bojinov persona non-grata, forbidding the player from entering the stadium or the training academy, due to his actions in a Taça da Liga match against Moreirense played the previous day.

He failed to score, infuriating the supporters and Sporting's managers, who subsequently banned Bojinov on the basis that he disrespected the decision of the coach and therefore the rules of the club.

[31] On the last day of January 2014, it was confirmed that Bojinov had signed with Bulgarian side Levski Sofia, the first time in his career he would play for a club in his home country.

He made his official debut for the club in a second qualifying round UEFA Champions League against Dila Gori on 14 July 2015.

[40] On 22 October 2015, Bojinov was in the starting XI against Athletic Bilbao in his first time 2015–16 UEFA Europa League group stage.

[49] He made his official debut for the club in the semi-final of the 2017–18 Croatian Football Cup against Dinamo Zagreb on 4 April 2018, coming on as a substitute in the 78th minute.

[51] Bojinov played for Levski Sofia during the spring of 2019, scoring the decisive playoff goal against Etar that helped the team qualify for the UEFA Europa League.

His time at the "bluemen" was sandwiched between two spells with Botev Vratsa - one in the second half of 2018, during which he established himself as an important player for the club, and a short, disappointing stint in the autumn of 2019.

[61] On 17 November 2005, Bojinov scored a goal against Mexico in a friendly match in the United States at NRG Stadium, contributing to a 3–0 win.

[62] On 6 September 2006, Bojinov scored his first international goal in a competition match, against Slovenia, in 3–0 home win in UEFA Euro 2008 qualifying.

Once considered to be a highly promising prospect in his youth, Bojinov is known for his skill and goalscoring abilities as a striker, and is capable of scoring with either foot, due to his powerful and accurate striking ability, which also enabled him to play alongside another forward as a second striker, or as winger on either flank, as well as in the centre of the pitch; a fast footballer in his prime, he was also known for his speed over short distances, agility, and explosive acceleration, as well as his quick feet, and close control in limited spaces.