On the eve of their meeting in the finals at the 2017 US Open, it emerged that as a 12-year old, Anderson regularly competed against future world number one Rafael Nadal on the juniors circuit.

In the championship dual match, Anderson lost at #1 singles to future ATP top-ten player, John Isner.

During the singles tournament, Anderson lost in the semifinals to eventual two-time national champion, Somdev Devvarman of Virginia.

At age 19, Anderson continued to play at the Futures level, exclusively in the United States, reaching the semifinals of USA F21 in August.

Anderson began 2008 with a bit of success, reaching the quarters of the Challenger in New Caledonia before qualifying in his first Grand Slam attempt in Australia.

At the 2008 Tennis Channel Open in Las Vegas, as a qualifier, he managed to defeat sixth seed Michaël Llodra in straight sets, 6–2, 7–6.

In the second round of the Sony Ericsson Open in Key Biscayne, Florida, he beat Novak Djokovic for his first win against a top-10 player.

At Wimbledon, Anderson and partner Robert Lindstedt of Sweden reached the quarterfinals before losing to the eventual tournament champions, Daniel Nestor and Nenad Zimonjić.

[9] Anderson advanced to the semifinals of the 2010 Atlanta Tennis Championships in July, upsetting fifth seed Janko Tipsarević in the first round.

He qualified and reached the third round of the Rogers Cup in Toronto, beating Leonardo Mayer and Sam Querrey before losing to no.

He then won his first Grand Slam match at the US Open over Somdev Devvarman in straight sets and backed it up with a five-set win over 26th seed Thomaz Bellucci.

At the Atlanta Tennis Championships, Anderson reached the quarterfinals as the second seed, defeating Michael Russell, before losing in straight sets to Gilles Müller.

At the 2011 Rogers Cup, he defeated Pablo Andújar in straight sets before beating an out-of-sorts Andy Murray in the second round with an easy victory.

[11] Anderson started the year at the Sydney International, where he reached the final, but lost to Australian Bernard Tomic in three sets.

Anderson started the year by reaching the fourth round of the Australian Open, before being knocked out in straight sets by Tomáš Berdych.

He repeated his success of 2013 by again reaching the fourth round in the French Open, before losing to fifth seed David Ferrer in four sets.

Anderson exited the Australian Open early in the first round and was advised to take some time off to sort out problems with his shoulder.

Anderson won his first-round match against Feliciano López, but lost in the second round to Juan Mónaco, despite winning the first set.

In Houston, he played doubles with Sam Querrey, making it to the semifinals before losing to Dustin Brown and Frances Tiafoe.

He then traveled to Barcelona, where he got past Carlos Berlocq and David Ferrer, losing in the third round to eventual champion Rafael Nadal.

He had his best result at the Citi Open in Washington, where he defeated Dominic Thiem in the second round and Jack Sock in the semifinals to earn a runner-up finish against Alexander Zverev.

All of his matches went to three sets; his path to the final included beating American rising star Frances Tiafoe and 2014 US Open finalist Kei Nishikori.

He reached the quarter-finals at the first two Masters 1000 events of the year, Miami and Indian Wells, losing to Borna Ćorić and Pablo Carreño Busta respectively, both times in a third set tiebreak.

Anderson saw a strong start to the hard court season at the Rogers Cup, defeating fifth seed Grigor Dimitrov in the quarterfinals before losing in three close sets to Stefanos Tsitsipas in the semifinals.

[25] He was then seeded sixth at the Miami Open and progressed into the quarterfinals, where he was defeated in straight sets by in-form and eventual champion Roger Federer.

[34] Anderson rebounded from his knee surgery and won his 7th ATP title at the Hall of Fame Tennis Championships by defeating Jenson Brooksby 7–6, 6–4.

However, due to Matteo Berrettini withdrawing from the tournament because of a right hand injury, he entered the main draw as a lucky loser.

[44][45][46] Anderson announced he was coming out of retirement, and in July he was awarded a wildcard for the 2023 Hall of Fame Open in Newport, Rhode Island.

Anderson prefers to play aggressively, taking control of rallies early and looking to finish points quickly.

[50] Anderson married his college girlfriend, golfer Kelsey O'Neal, in 2011, and they bought a home in Delray Beach, Florida.