He began his playing career as a teenager with his hometown club Cardiff City, becoming the youngest player to make an appearance for the side when he made his debut in 1965.

[4] He resigned from Swansea in 1984 after suffering relegation and embarked on a managerial career abroad, taking charge of Sporting CP in Portugal and later Spanish side Real Sociedad, winning the Copa del Rey in 1987.

Two years later, he was appointed manager of Real Madrid and led them to a fifth consecutive La Liga title with a record total of points and goals scored.

After a spell in Turkey with Beşiktaş, he returned to Real Madrid for a second time but was sacked ten months later after refusing to retract criticism he had made of his players in a press conference following a defeat.

[14] His performance during his debut persuaded manager Jimmy Scoular to promote him to the starting line-up for the following match and Toshack found the net again, scoring a brace during a 4–3 victory over Middlesbrough.

[15] He scored his first career hat-trick in January 1968 in an 8–0 win over Ebbw Vale in the Welsh Cup,[12] and went on to form one of the most prolific partnerships in the club's history alongside Brian Clark.

Cardiff manager Scoular and board member George Edwards both opposed the transfer, but were unable to convince chairman Fred Dewey to block the move.

[16] The deal was completed on 11 November 1970, Liverpool manager Bill Shankly paying £111,000 for the striker,[16] a club record fee at the time.

[16] Liverpool had resurrected a potential deal for Toshack after an attempt to sign Huddersfield Town forward Frank Worthington collapsed after he failed a medical.

In his first season at Anfield, Toshack scored seven times in all competitions but his noted aerial ability proved to be a key asset in Liverpool's style of play as it helped the side reach the 1971 FA Cup Final, losing 2–1 to Arsenal.

[24] Don Revie's Leeds United visited Anfield on Easter Monday for a match involving two of the three 1972–73 Football League title challengers.

To exploit this, he brought tall forward Toshack into the starting team demoting the small build of Brian Hall to appearing only as a late substitute.

[28] However, the deal later collapsed after he failed a medical and, at the age of 25, Toshack was told by specialist doctors that he only had around twelve months left to play due to mounting injuries.

He ended his medal haul with a further league title in 1977 but increasing injury concerns limited his appearances and a proposed £60,000 transfer to Belgian side Anderlecht broke down after a medical discovered calcification in some muscle tissue.

[36][38] He overhauled numerous aspects of the club's day-to-day routine including changing players' diets, moderating their alcohol intake and revising travel arrangements for away matches.

[37] The following season, Toshack convinced several of his former Liverpool teammates, such as Ian Callaghan, Phil Boersma and Tommy Smith, to join the club.

"[37] Once they reached the top flight, Swansea were predicted by many to be relegated, but in their first match in the First Division they claimed a 5–1 victory over Leeds United after a hat-trick from newly arrived club-record signing Bob Latchford.

[40] In 1984, Toshack was appointed manager of the Portuguese side Sporting CP, but he only lasted one season in the post, during which he led the team to second place in the league.

[42] He instead moved to Spain, taking a position as manager of Real Sociedad where he led the side to victory in the 1986–87 Copa del Rey and were the league runners-up in 1988.

[45] Nevertheless, Toshack strengthened defensively by adding Oscar Ruggeri and Fernando Hierro to the club's ranks, but endured a difficult start after losing to rivals Barcelona and being eliminated from the European Cup in the second round; he was also under pressure from local press, despite leading the La Liga table after ten matches.

[45] A disappointing start to the following season and a three-match losing streak led to him being sacked by the club after eleven matches in November 1990 and he returned to Sociedad,[46][47] initially in an advisory role, before taking charge soon after.

[49] In 1994, Toshack was appointed as manager of the Wales national team on a part-time basis, taking the job alongside his position in charge of Sociedad, after approaches for Terry Venables and Bobby Robson were rejected.

[51] He was appointed to succeed Terry Yorath, who had narrowly missed out on qualification to the 1994 FIFA World Cup and had expressed his desire to remain in the role but was not offered a new contract by the Football Association of Wales (FAW).

With support for Yorath still strong among Welsh fans over his dismissal by the FAW, a disappointing performance against Norway saw the team jeered off at both half and full-time and Toshack resigned from the role after just 47 days in charge.

However, the start of the following season saw Madrid again struggle and, following a 3–2 defeat to Rayo Vallecano that left them in eighth position, Toshack publicly criticised his players, particularly Albano Bizzarri commenting that the goalkeeper conceded goals "that made me weep".

[56] Toshack claimed that his words were meant as a motivational tactic and refused club president Lorenzo Sanz's request that he withdraw his comments, saying "there's more chance of a pig flying over the Bernabeu".

He then had short spells with Italian team Catania from November 2002 to January 2003, in a calamitous season for the club in which it got relegated from the Serie B in a scandal known as "Caso Catania" before the decision was reversed in August 2003; this preceded another return to Spain with last–placed La Liga side Real Murcia in January 2004, failing to save the club from relegation.

[8] In his first full qualifying campaign, Toshack's squad was plagued by withdrawals, so much so that he chose to issue a letter to 36 Welsh players for them to show "total commitment to the cause".

[75] Eleven months after resigning from his role with Wales, Toshack was appointed manager of the Macedonia national football team on 7 August 2011.

[80] Khazar Lankaran ended the season in eighth position, with a league record under Toshack of three games out of nine won, with an equal number of three matches drawn or lost.