At the Dubai Tennis Championships, he beat Andreas Seppi in the opening round,[12] and then stunned third seed Andy Murray in three sets, for the best win of his career to that point.

He beat Jérémy Chardy, Arnaud Clément, Peter Luczak, and defending champion Benjamin Becker en route, only to lose to in-form Sergiy Stakhovsky in two sets.

After the US Open, Tipsarević scored key wins over Tomáš Berdych and Radek Štěpánek in the Davis Cup for Serbia, filling in for an ill Novak Djokovic.

Tipsarević then played the Miami Masters, reaching the fourth round on a run where he defeated Robin Haase, Marin Čilić, and Philipp Petzschner, before losing to Gilles Simon.

He defeated Kei Nishikori, Mischa Zverev, and Somdev Devvarman, before he withdrew in his match with countryman Novak Djokovic.

At Roland Garros, he reached the third round, defeating Brian Dabul and Pere Riba in straight sets before losing to Roger Federer.

His next event was the Queen's Club Championships where he reached the round of 16, defeating Blaž Kavčič and Michael Russell before losing to Andy Murray in two sets.

He defeated James Ward, Mikhail Kukushkin, Grigor Dimitrov, and Kei Nishikori, before losing to Andreas Seppi, retiring hurt at 3–5 in the third set.

His form improved at the Legg Mason Tennis Classic, where he reached the quarterfinals, defeating Michael Berrer and Grigor Dimitrov, but lost to eventual finalist Gaël Monfils in straight sets.

At the Rogers Cup, Tipsarević had an impressive run, defeating Alejandro Falla, Fernando Verdasco, Ivan Dodig, and Tomáš Berdych to reach his first Masters series semifinal, where he lost to Mardy Fish.

In the Davis Cup semifinal showdown between Serbia and Argentina, Tipsarević was defeated in three straight sets by Juan Martín del Potro during the second singles rubber of the tie.

Tipsarević suffered first-round exits at the Japan Open to Dmitry Tursunov,[16] and at the Shanghai Masters to Feliciano López.

In the first all-Serbian final in tennis history, Tipsarević defeated his good friend, compatriot, and defending champion Viktor Troicki in two sets, to win his second career title.

Tipsarević represented Serbia in the Davis Cup quarterfinal clash with the Czech Republic, which was played on clay in Prague.

At the first ATP Master Series 1000 clay event of 2012 in Monte Carlo, he defeated Albert Montañés, before losing to Gilles Simon in three sets in the third round.

At the Madrid Open, he defeated Federico Delbonis in the first round, before avenging his loss to Gilles Simon by beating him for the first time in five meetings.

[21] At the Rogers Cup, he got past Mikhail Youzhny, Marin Čilić, and Marcel Granollers to reach his third Masters semifinal, but fell to Djokovic in two sets.

Tipsarević began his season by going one step better than the previous year to lift the 2013 Aircel Chennai Open title, defeating surprise finalist Roberto Bautista Agut in the final.

[25] At the Australian Open, he defeated Lleyton Hewitt, Lukáš Lacko and Julien Benneteau to reach a career-best fourth round of that tournament.

[27] Following 17 months of inactivity, Tipsarević made a return to the ATP World Tour, stating: "My goal and dream would be to come back to the top 10, and I don’t have many weeks to waste.

"[28] He began his season in March, partnering Djokovic in doubles at the Miami Masters, which Tipsarević had entered using a protected ranking (PR).

In April, Tipsarević received a wild card for the U.S. Clay Court Championships in Houston, where he saved two match points to defeat qualifier Guilherme Clezar in the opening round.

At the BMW Open he defeated Bernard Tomic (world 27), before being halted by Víctor Estrella Burgos Next, in May, he was given a wildcard for the Masters Madrid event qualifying draw.

He suffered first round exits at Roland Garros and Wimbledon, however in August his season built serious momentum when he won the China International Challenger.

In 2010, he was the hero in steering the Serbian team into their first historic Davis Cup final after prevailing over Radek Štěpánek to complete the 1–2 come-from-behind victory to help clinch the tie 3–2 over the Czech Republic.

Before the match against Canada, Tipsarević together with Novak Djokovic, Nenad Zimonjić, and Slobodan Živojinović received their Davis Cup Commitment Award, which is granted to players who have shown long-standing dedication to representing their country in the competition.

[30] Janko is or was sponsored in the past by Tecnifibre, Fila, Oakley, Tennis Flex, Extreme Intimo,[31] Trion:Z/Colantotte, Instaforex, Telekom Srbija.

3 Including appearances in Grand Slam and ATP World Tour main draw matches, and in Summer Olympics.

[36] During Tipsarević's professional tennis career, match commentators and press often brought up the player's love of classic literature as something unusual for a high-level athlete.

[40] They married on 4 July 2010 in a civil ceremony at the S-Club hospitality venue in Jakovo with 300 guests in attendance, including Tipsarević's Davis Cup teammates Novak Djokovic, Viktor Troicki, and Nenad Zimonjić.