Sousa began the 2014 season with a first-round loss at the 2014 Qatar Open.
At the Sydney International's doubles competition, he partnered with Lukáš Rosol to defeat the Bryan brothers, the then-world No.
 1 doubles team, en route to the semifinals.
At the 2014 Australian Open, he was beaten by world No.
 137 Dominic Thiem in the first round.
Partnering with Colombian Santiago Giraldo, Sousa was eliminated in the first round of the doubles competition by Mahesh Bhupathi and Rajeev Ram.
Later in January, Sousa joined the Portugal Davis Cup team to face Slovenia for the Europe/Africa Group I 1st Round.
He won his first singles match against Janez Semrajc, but then lost in the doubles match and his second singles match against Blaž Kavčič.
Portugal eventually lost 3–2 and fell to a relegation playoff.
In February, he started with early round losses at the Open Sud de France and ATP Buenos Aires.
Sousa played at the Rio Open and reached the quarterfinals, where he was beaten by world No.
 1 Rafael Nadal.
Sousa ended February with a second-round defeat and exit to Andy Murray at the Mexican Open.
During the North American hard court Masters swing in March, Sousa started the Indian Wells Masters with a win over Aleksandr Nedovyesov, followed with a second-round loss to 20th seed Ernests Gulbis.
At the 2014 Sony Open Tennis in Miami, Florida, Sousa  reached the third round.
After beating 26th seed Gilles Simon in the second round, he lost to world No.
 7 Tomáš Berdych.

Sousa began the spring clay court season at the Grand Prix Hassan II in Casablanca, where he was beaten by world No.
 273 Roberto Carballés Baena in a second-round match lasting over three hours.
This loss started an eight-match losing streak that lasted the remainder of the clay court season – it included losses at the Monte-Carlo Masters, at the Barcelona Open, at the Portugal Open, at the Madrid Masters, at the Rome Masters, and at the Düsseldorf Open.
In the first round of the 2014 French Open, Sousa suffer his eighth consecutive loss against world No.
 2 Novak Djokovic.
During this run of losses, Sousa reached the semifinals of the Portugal Open's doubles competition and the third round at the 2014 French Open doubles competition, where he partnered with American Jack Sock and lost to Andrey Golubev and Sam Groth.

Sousa made his debut at an ATP grass tournament main draw at the Halle Open.
In the first round, he beat German wild card Jan-Lennard Struff and snapped the eight match losing streak.
Then, he faced former world No.
 1 and 6-time Halle champion Roger Federer in the second round.
After winning a close first set, Sousa ended up losing in three sets to the Swiss.
At the Rosmalen Grass Court Championships, Sousa became the first Portuguese player ever to reach the semifinal of an ATP tour level grass tournament.
He beat in succession Paolo Lorenzi, Mate Pavić and Thiemo de Bakker, losing in the semifinals to Benjamin Becker.
To cap his grass court season, Sousa played his first ever Wimbledon Championships main draw match at the 2014 edition, with a straight sets loss in the first round to world No.
 3 Stan Wawrinka.
In the doubles competition, he partnered with Argentinian Carlos Berlocq to play a four-hour, five-set first round loss to Martin Kližan and Dominic Thiem.

In July, Sousa reached his second-career ATP tour level final and his first of 2014 at the Swedish Open, defeating the defending champion Carlos Berlocq in the semifinals.
He lost the final to the Uruguayan Pablo Cuevas in straight sets.
After losing in early rounds at the German Open and the Croatia Open, Sousa entered the Canada Masters, where he was defeated in the first round by 11th seed Gulbis.
At the Cincinnati Masters, Sousa was defeated by Andy Murray in the second round.
Sousa was also eliminated in the second round of the Winston-Salem Open.
At that tournament's doubles competition, Sousa reach his third semifinal of the season, teaming up with Romanian Florin Mergea.
At the 2014 US Open, Sousa became the first Portuguese player to be seeded at a Grand Slam tournament, with the 32nd
Sousa began the 2014 season with a first-round loss at the 2014 Qatar Open. At the Sydney International's doubles competition, he partnered with Lukáš Rosol to defeat the Bryan brothers, the then-world No. 1 doubles team, en route to the semifinals. At the 2014 Australian Open, he was beaten by world No. 137 Dominic Thiem in the first round. Partnering with Colombian Santiago Giraldo, Sousa was eliminated in the first round of the doubles competition by Mahesh Bhupathi and Rajeev Ram. Later in January, Sousa joined the Portugal Davis Cup team to face Slovenia for the Europe/Africa Group I 1st Round. He won his first singles match against Janez Semrajc, but then lost in the doubles match and his second singles match against Blaž Kavčič. Portugal eventually lost 3–2 and fell to a relegation playoff. In February, he started with early round losses at the Open Sud de France and ATP Buenos Aires. Sousa played at the Rio Open and reached the quarterfinals, where he was beaten by world No. 1 Rafael Nadal. Sousa ended February with a second-round defeat and exit to Andy Murray at the Mexican Open. During the North American hard court Masters swing in March, Sousa started the Indian Wells Masters with a win over Aleksandr Nedovyesov, followed with a second-round loss to 20th seed Ernests Gulbis. At the 2014 Sony Open Tennis in Miami, Florida, Sousa  reached the third round. After beating 26th seed Gilles Simon in the second round, he lost to world No. 7 Tomáš Berdych.
Sousa began the spring clay court season at the Grand Prix Hassan II in Casablanca, where he was beaten by world No. 273 Roberto Carballés Baena in a second-round match lasting over three hours. This loss started an eight-match losing streak that lasted the remainder of the clay court season – it included losses at the Monte-Carlo Masters, at the Barcelona Open, at the Portugal Open, at the Madrid Masters, at the Rome Masters, and at the Düsseldorf Open. In the first round of the 2014 French Open, Sousa suffer his eighth consecutive loss against world No. 2 Novak Djokovic. During this run of losses, Sousa reached the semifinals of the Portugal Open's doubles competition and the third round at the 2014 French Open doubles competition, where he partnered with American Jack Sock and lost to Andrey Golubev and Sam Groth.
Sousa made his debut at an ATP grass tournament main draw at the Halle Open. In the first round, he beat German wild card Jan-Lennard Struff and snapped the eight match losing streak. Then, he faced former world No. 1 and 6-time Halle champion Roger Federer in the second round. After winning a close first set, Sousa ended up losing in three sets to the Swiss. At the Rosmalen Grass Court Championships, Sousa became the first Portuguese player ever to reach the semifinal of an ATP tour level grass tournament. He beat in succession Paolo Lorenzi, Mate Pavić and Thiemo de Bakker, losing in the semifinals to Benjamin Becker. To cap his grass court season, Sousa played his first ever Wimbledon Championships main draw match at the 2014 edition, with a straight sets loss in the first round to world No. 3 Stan Wawrinka. In the doubles competition, he partnered with Argentinian Carlos Berlocq to play a four-hour, five-set first round loss to Martin Kližan and Dominic Thiem.
In July, Sousa reached his second-career ATP tour level final and his first of 2014 at the Swedish Open, defeating the defending champion Carlos Berlocq in the semifinals. He lost the final to the Uruguayan Pablo Cuevas in straight sets. After losing in early rounds at the German Open and the Croatia Open, Sousa entered the Canada Masters, where he was defeated in the first round by 11th seed Gulbis. At the Cincinnati Masters, Sousa was defeated by Andy Murray in the second round. Sousa was also eliminated in the second round of the Winston-Salem Open. At that tournament's doubles competition, Sousa reach his third semifinal of the season, teaming up with Romanian Florin Mergea. At the 2014 US Open, Sousa became the first Portuguese player to be seeded at a Grand Slam tournament, with the 32nd
João Sousa