Ivanišević made his first significant impact on the tour in 1990, knocking Boris Becker out of the first round of the French Open men's singles; he went on to reach the quarterfinals.

In 1992, Ivanišević surged his way into his first Wimbledon singles final, having defeated Ivan Lendl, Stefan Edberg, and Pete Sampras in succession.

Later that summer at the Olympic Games in Barcelona, Ivanišević won bronze medals in both singles and doubles representing Croatia, a state that had only recently declared independence;[17][18] he also served as flagbearer for the Croatian team at the opening ceremony.

He returned to tennis sparingly in the following years but, in 2004, retired after a third-round loss to Lleyton Hewitt at Wimbledon, held on the Centre Court, the scene of his greatest triumph.

[36] Ivanišević also participated in an exhibition match of the Croatian national team of 1998 versus the International football stars on 7 October 2002 in Zagreb.

Ivanišević received a winner's medal and his name was engraved on the trophy along with Mario Ančić, Ivo Karlović, Ivan Ljubičić and team captain Nikola Pilić.

In November of the same year, Ivanišević won the Merrill Lynch Tour of Champions tournament in Frankfurt, defeating John McEnroe 7–6(12), 7–6(1).

Retiring in 2004 also allowed thirty-three-year-old Ivanišević to devote more attention to investing in the real estate and construction industries, which he had already been involved with since 1998, conducting the activities through the simultaneously registered Sport Line limited liability company based in Split, Croatia.

Due to Ivanišević still being an active tennis player at the time of the venture's launch, most of the company's initial day-to-day business was handled by his father Srdjan.

[39] News of Ivanišević's financial problems first appeared in the summer of 2005 after he talked about it in an interview with Globus newsmagazine, revealing Lazarica 2 to be a "failed project",[40][41] as well as admitting to being "devoured by sharks" after hastily getting into investments that in hindsight he viewed as "jumping overnight from kindergarten to university".

[45] By September 2006, after months of speculation,[46][47] Ivanišević joined a group of investors—including active AC Milan footballer Dario Šimić, retired basketball player Ivica Žurić as well as businessmen Marijan Šarić, Mate Šarić, and Batheja Pramod—for a joint HRK93 million (~€12.5 million) investment into the added market capitalization of Karlovačka banka.

[51] On 31 January 2013, after accumulating debts of HRK5.7 million (~€752,000), Ivanišević's company Sport Line filed for bankruptcy settlement proceedings before the Croatian Trade Court.

[52] Additionally, even his real estate business, conducted through another limited liability company, Goran promocije, was in trouble, with its account blocked for over a year with debts of HRK1.14 million.

[53][54] According to Croatian media reports, as of his company's 2013 bankruptcy proceedings, most of Ivanišević's assets—such as his two Zagreb apartments, his ownership stake in Karlovačka banka, and his 40,000 m2 of land in Duilovo—were safe from being sold off or liquidated as he had already signed them over to either his wife Tatjana Dragović (the Zagreb apartments and bank stake) or his mother Gorana Ivanišević (the plot of land).

[54][55][53] Soon after his memorable 2001 Wimbledon win and the next day's rapturous hero's homecoming with 150,000 people coming out to greet him in the Split harbour, Ivanišević purchased a derelict seaside property within the Marjan hill park/forest in the neighbourhood of Meje adjacent to the city centre.

[56] Despite the city of Split urban development plan intending the attractively located area by the sea in Meje for public use, the tennis player successfully petitioned the city authorities into changing their plan thus opening the door for tearing down the existing dilapidated structure and instead building a private use 1,000 m2 modernist villa, which Ivanišević claimed would become his family home once he retires from playing tennis professionally.

[57] In his 2001 application submission to the Split city council, the Wimbledon champion tied the two construction projects together, asking to be allowed to build a private-use property in Meje while promising to "give back to the citizens of Split and Croatian sports" by building a youth tennis academy on the plot of land in Duilovo.

By 2006, the construction of the new 1,500 m2 three-storey, five-bedroom villa designed by his relative, architect Vjeko Ivanišević on a 1,560 m2 plot of land was completed with extensive amenities such as an indoor and outdoor pool, Jacuzzi, sauna, weight room, and wine cellar.

[58][59] During the villa's early-to-mid 2000s construction, when not in tournaments, Ivanišević (an active professional tennis player until 2004) spent most of his time in Zagreb where he had already been owning multiple residential properties.

However, even after retiring in 2004, contrary to his earlier pronouncements, he never moved into the Split villa once it was complete in 2006, instead continuing to reside in Zagreb with his model girlfriend Tatjana Dragović.

[58] The move instantly provoked angry reactions in the Croatian public and Split-based media outlets with accusations of "exploiting his hometown hero status" and "not only emotionally blackmailing his fellow Splićani but also outright lying to them" being directed at Ivanišević.

[60][61] After more than four years on the market and multiple re-listings with a lower asking price[62][63]—including being offered in 2010 through the British real estate agency Savills that advertised it in the English press during fall 2010 as a high-end weekend escape property[64][65]—the villa (that had been listed for HRK31 million as of summer 2011)[66] was in May 2012 sold to the Hvar-born, Russia-based Croatian businessman Stefano Vlahović for an undisclosed amount widely speculated to be less than half of the amount Ivanišević originally asked for.

[69] In June 2013, in the wake of Marin Čilić's doping-related nine-month suspension that came into effect in the middle of his 2013 Wimbledon participation, the player reached out to his compatriot Ivanišević to become his new coach.

[72] In February 2018, the 31st-ranked ATP player and 2016 Wimbledon finalist Milos Raonic—having had his 2017 season marked by prolonged layoffs due to wrist and knee injury issues in addition to just coming off being eliminated from the Australian Open in a first round upset to unseeded Lukáš Lacko—looked to hire a new coach by holding separate trials with Jonas Björkman during the Delray Beach Open and Ivanišević during the Indian Wells Masters.

Discussing his initial week-long interaction with Djokovic, Ivanišević praised the player's "perfectionism", stating to have felt "wanted as a coach for the first time in a long time" while simultaneously experiencing the "pleasure of coaching an individual that asks questions and actually listens to and processes what you have to say" and adding that he has "tragically had a more meaningful and worthwhile communication with Djokovic in an hour than with Raonic in the entire year".

[91][92][93][94] Claiming to be speaking up out of "human and moral obligation to our greatest heroes", the 11 athletes express being horrified at the Croatian government's decision to hand over war crimes suspects, seeing it as an attempt to "distort historical facts" before concluding that the "one and only truth is that Croatia was a victim [in the Yugoslav Wars] while its soldiers and generals were heroes".

[91][93][94] Among the other Croatian athletes that signed the letter were Zvonimir Boban, Alen Bokšić, Davor Šuker, Slaven Bilić, Igor Štimac, Aljoša Asanović, Dino Rađa, and Stojko Vranković.

[91][92][93] The letter caused immediate reaction in Croatia, including Science and Higher Education Union [hr] (NSZ) sarcastically dismissing the signatories as "pro athletes on their yachts and in their Ferraris [who] would certainly not be feeling the pain of resulting international political and economic sanctions inflicted upon Croatia were it to refuse co-operation with the ICTY".

[96][97] At a late June 2007 rally at the Dražen Petrović Basketball Hall, where he arrived with his pregnant girlfriend Tatjana Dragović, Ivanišević addressed the crowd using tennis analogies: "Over the previous 4 years, we [Croatia led by Sanader and the HDZ] learned the backhand, forehand, and baseline play; and in the last 10 years we've mastered the serve; now, we have to learn net play by being accepted into the European Union".

[98][99][100] Also endorsing the HDZ on this campaign trail were other prominent Croatian sporting figures such as retired basketball star Dino Rađa, active footballers Niko Kovač and Tomislav Butina, retired water polo player Zdeslav Vrdoljak, retired basketball players Franjo Arapović and Stojko Vranković, handball coach Lino Červar, retired handballer Slavko Goluža, football administrators Zdravko and Zoran Mamić, boxer Stipe Drviš, active water polo players Teo Đogaš, Mile Smodlaka, and Josip Pavić, and active handballers Ivano Balić, Petar Metličić, and Renato Sulić.