Holebas was born in Aschaffenburg, West Germany, to a Greek father, Achilles, from Vasiliki, Trikala, and a German-American mother, Lowis.

A year later, in 2002 and with the guidance of his German-American uncle, Alfonso, whom Holebas described as his "second father" and "who gave me the kicks I needed to get my life back on track," helped him begin playing football again.

[7] In his first season in Munich, Holebas was in 1860's second team, where, at 22 years of age, he was considered "too old" by the club's youth academy coach, Ernst Tanner.

Holebas finished his five-season stint in Germany with both Viktoria Kahl and 1860 Munich, scoring a total of 34 goals in 154 games in all competitions.

On 15 July 2010, Holebas made his debut for Olympiacos in a 5–0 away victory over Albanian club Besa Kavajë in the first leg of a Europa League second qualifying round tie.

On 5 August, Olympiacos were knocked out of the UEFA Europa League by Israeli club Maccabi Tel Aviv, on the away goals rule and after a 2–2 draw.

On 19 October 2011, Holebas opened the score with a header against Borussia Dortmund in a 3–1 home victory on matchday 3 of the Champions League group stage.

The Turks reportedly offered the 29-year-old defender a three-year contract, with an annual salary reaching €750,000, a significant pay rise than what he was being paid by Olympiacos.

"[13] On 24 September 2014, Holebas made his debut for the club, by playing the full 90 minutes in a 2–1 away league victory over Parma in their fourth match of the 2014–15 Serie A.

[14] On 30 November, Holebas scored his first goal for Roma in an important 4–2 home victory over Internazionale in their 13th match of Serie A to stay in touch with the top of the table.

On 25 June 2015, it was reported that recently promoted Premier League club Watford were close to securing a deal for Holebas after the side confirmed interest by contacting the Italians and admiring the player's profile; they allegedly offered between €2–3 million for his services.

At that point, there was a summit at Trigoria between Roma Sporting Director Walter Sabatini and the entire staff, including head coach Rudi Garcia and Simone Beccaccioli.

[22] On 24 March 2016, radio station Radyospor reported that Holebas had been offered to Turkish giants Fenerbahçe, as a potential replacement for Caner Erkin if the latter left at the end of the season.

[28] On 2 September 2018, Holebas helped his club to maintain their perfect start to the Premier League season, setting up goals for Troy Deeney and Craig Cathcart in a 2–1 home win against Tottenham.

[31] On 12 May 2019, in the last matchday of the season and his 100th match in Premier League, West Ham's winger Michail Antonio causing the problems, outpacing the Greek left back onto Felipe Anderson's through ball, and the former Greek international tugs him back receiving a straight red card, that will keep him away of the FA Cup final, in a hammering 4–1 home loss against West Ham, but a day later Holebas will be available for the FA Cup final against Manchester City after his red card was rescinded.

The vastly experienced left-back, now 36 years of age, has been signed as a replacement for Konstantinos Tsimikas who recently joined Liverpool and in overall he participated in 114 Premier League games, contributing with six goals and 14 assists.

[37] In September 2021, Holebas decided to leave professional football and accepted the offer of his close friend, coach-player Peter Sprung, signing a contract with Hessenliga club Bayern Alzenau and at the same time continue the lessons for obtaining UEFA coaching diplomas.

In November 2011, he received Greek citizenship as "Iosif Cholevas,"[39] and on the 11th of the same month, he officially made his debut for Greece in a friendly match against Russia, which ended in a 1–1 draw at the Georgios Karaiskakis Stadium in Piraeus.

He started the first two group games against Poland in a 1–1 draw and against Czech Republic in a 2–1 loss and was dropped for the third match due to heavy criticism that his attacking tendency was becoming hazardous to the usually-solid defensive tactics of Greece.

Here, however, Greece fell to Germany by a score of 4–2, a defeat in which Holebas picked up a suspension for receiving another yellow card after his previous booking in the game against Russia.

[40] Holebas scored his first international goal for Greece in a 1–0 victory against the Republic of Ireland in November 2012, a friendly match played at the Aviva Stadium in Dublin.

Holebas' impressive 2013–14 season with Olympiacos prompted his nomination from Greek manager Fernando Santos as a part of the final 23-man squad for the 2014 FIFA World Cup in Brazil.

[41] On 27 March 2015, two days before the crucial Euro 2016 qualifier for Greece against Hungary, media reports claimed that Holebas had trained normally with his Roma squad after departing from Austria on Tuesday.

The player trained in Austria under an individual program but was not fit to be available to play against Hungary," the Hellenic Football Federation (HFF) said in an announcement.

The HFF added that reports out of Italy cited by the Greek media "lead to completely erroneous conclusions in regards to the willingness of the player to contribute to his commitments with the national team any further.

[44] In 2018 FIFA World Cup qualification, Holebas played his 38th and last ever cap for Greece when he came on as a second-half substitute in the Greek 2–0 home win over Cyprus on 7 October 2016 in Piraeus.