Genie Bouchard playing match at Wimbledon

Photo: Martin Sidorjak

It is the most prestigious and oldest tournament the world of tennis has to offer, and for Canadian players it has served (no pun intended) as a landmark event.

Some of the greatest achievements in Canadian sport have come on the grass courts of Wimbledon.

While the 2022 edition was not to be for Canada as none of its four singles competitors advanced past the second round, and Gaby Dabrowski lost in the mixed doubles quarterfinals, there are plenty of achievements to reflect on from year’s past.

Here are five incredible moments from Canadians at London’s All England Club:

Genie Bouchard’s 2014 finals run

Photo: Mauricio Paiz

Montreal’s Genie Bouchard was already a well established, rising player when she arrived to the All England Club in 2014.

She opened that season impressively with a breakthrough run to the Australian Open semifinals, earning a big win over Ana Ivanovic.

In the spring, she captured her first and only WTA singles title, defeating Karolina Pliskova in the finals of the Nuremberg Cup.

That great clay court result paved the way for a run at Roland Garros. Bouchard won five matches at the French Open and pushed eventual champion Maria Sharapova in a thrilling three-set semifinal encounter.

Flash forwards a month later to Wimbledon and Bouchard arrived confident and poised for a deep run. 

She promptly returned to yet another major semifinal by reeling off five wins, and then scored one of the biggest victories of her career, a 7-6(5), 6-2 triumph over Simona Halep.

Video: Wimbledon

While she fell to Petra Kvitova in a one-sided championship match, Bouchard made history by becoming the first Canadian to reach a Grand Slam singles final, and helped pave the way for many current and future tennis stars in the country.

She would close the season ranked a career high no. 5 and was named WTA’s Most Improved Player of the Year.

Milos Raonic reaching the 2016 Final

Photo: Mauricio Paiz

He possesses one of the world’s greatest serves, and while Milos Raonic has not been active on the circuit in the last year, he still has managed many exceptional achievements in the sport.

His greatest of all was on the grass courts of Wimbledon six seasons ago. 

Raonic had been compiling a great 2016 from the very first tournament of the season, as he opened his campaign with an ATP title in Brisbane, defeating Roger Federer in the final. 

The form continued on the hard courts of Melbourne, as he made the semifinals of the Australian Open, becoming the first Canadian man to reach that stage.

In March, he produced four consecutive top 20 wins en route to the finals of Indian Wells in California, before losing out on the title to Novak Djokovic.

By the time the grass court swing arrived in June, the Canadian was firmly established as a contender.

He made the finals of the Queen’s Club Championship in his lead-in tournament, beating talented grass players like Nick Kyrgios, Roberto Bautista Agut, and Jiri Vesely.

Thus, the stars were aligned for the Canadian to deliver some magic at London’s All England Club.

Raonic played almost flawlessly in the opening week of 2016 Wimbledon, winning his opening three matches in straight sets as he dismantled Pablo Carreno Busta, Andreas Seppi, and Jack Sock.

He was forced to dig deep in a round of 16 encounter against Belgian David Goffin, who’s pedigree and -experience make him a tough out on the circuit. Raonic rallied for a five-set victory.

A four-set win over American Sam Querrey set the stage for a semifinal showdown with the greatest Wimbledon champion of all: Roger Federer.

Raonic was unfazed by the occasion, and, on a packed Centre Court, went toe-to-toe with the all-time great.

Video: Wimbledon

The Canadian prevailed in the thriller 6-3, 6-7(3), 4-6, 7-5, 6-3 to reach his first career major final.  

“Mentally, I had one of the best matches of my career”, revealed Raonic after the win.

It was also significant as it marked the first time Federer had lost a semifinal at Wimbledon in 11 matches.

Though Raonic would lose to Andy Murray in straight sets in the title match, he notched a piece of his own history as the first Canadian man to reach the Wimbledon singles final. 

By the end of the year, Raonic had climbed to world no. 3, the highest singles ranking ever achieved by a Canadian in tennis history.

A Breakthrough semifinal from Denis Shapovalov

Photo: Martin Sidorjak

It was quite evident Denis Shapovalov loved the grass as a teenager.

At the age of 17, the Richmond Hill, Ontario native won the junior boys singles title at the All England Club in 2016, beating current professional and top 20 standout Alex de Minaur in the finals.

One year later and Canadians would see Shapovalov’s professional career catapult in the summertime.

While he competed and lost in the first round of Wimbledon in 2017, he’d electrify crowds later that summer at the National Bank Open (formerly Rogers Cup) with a monumental upset of Rafael Nadal and reach the semifinals of the tournament.

By 2019, Shapovalov had his first ATP title, and the following season he reached the top 10 and made the quarterfinals of the US Open.

Just a season ago, Shapovalov held the 10th seed heading into the 2021 Wimbledon Championships and promptly caught fire.

The streaky left hander flashed aggressive, quick strike grass tennis to navigate the first week with ease.

After beating two-time Wimbledon champion Andy Murray in the third round, he easily dispatched Spanish veteran Roberto Bautista Agut in straight sets to charge into the quarters.

Shapovalov would dig especially deep in his next encounter, overcoming Karen Khachanov 6-4, 3-6, 5-7, 6-1, 6-4 in 3 hours, 26 minutes to advance to his maiden grand slam semifinal.

The Canadian struck 59 winners in the match, a testament to his aggressive game style.

Video: Wimbledon

Novak Djokovic would end his campaign in the semifinals with a 7-6(3), 7-5, 7-5 victory and a match later hoist his sixth Wimbledon crown.

However, the experienced gained from the run at the All England Club should act as a personal reminder to Shapovalov of the type of brilliant level and quality he is capable of on the biggest of stages. 

Pospisil’s 2014 doubles crown

Photo: Martin Sidorjak

While BC native Vasek Pospisil has always been a proficient singles player, with a career high ranking of 25, he holds his greatest accolades in the sport in doubles.

Pospisil excels with a booming first serve and great hands at net, and entering the 2014 Wimbledon campaign, he found himself the perfect partner in crime in American Jack Sock.

The pair, competing in their first tournament together, delivered vintage doubles tennis during the fortnight at the All England Club, advancing to the finals where they’d encounter the greatest tandem of all in brothers Bob and Mike Bryan.

While the Bryan brothers were seeking a 16th grand slam doubles crown, Pospisil and Sock completed a remarkable Cinderella story, as they stunned the defending champions 7-6(5), 6-7(3), 6-4, 3-6, 7-5 in a 3-hour, six-minute epic.

The following month Pospisil would again play alongside Sock as the two won the ATP Atlanta Open, and then reached the finals in Cincinnati before losing to the Bryan brothers in a Wimbledon rematch.

Pospisil would achieve a career best run at a major in singles a year later, advancing to the Wimbledon quarterfinals.

Back-to-back Wimbledon titles from Daniel Nestor

Toronto’s Daniel Nestor is one of the most decorated doubles champions in tennis history.

He’s the owner of 91 men’s doubles titles, of which 8 are men’s doubles in Grand Slams, 4 are mixte doubles in Grand Slams, 4 are from the Year-End tournament, 1 Olympic Gold, and 28 are from Masters 1000 events.

He was also the first doubles player in ATP Open Era history to win 1,000 matches, accomplishing the immense feat in 2016.

While Nestor produced success early in his career, winning his first major title at the 2002 Australian Open, arguably his strongest run of doubles tennis came in 2008-2009 on the grass courts of the All England Club.

After several years competing alongside Bahamian partner Mark Knowles and winning the Australian Open, US Open, and French Open, Nestor joined forces with Serbia’s Nenad Zimonjic at the end of his 2007 season. 

The partnership produced early dividends almost immediately as the pair made finals runs at Indian Wells, Rome, Roland Garros, and won a Masters 1000 title in Hamburg.

The one major title that had always alluded Nestor was Wimbledon. 

The pair, seeded second at the All England Club, managed outstanding tennis on the grass courts in 2008, and despite Zimonjic nursing a wrist injury, prevailed over Sweden’s Jonas Bjorkman and Kevin Ullyet of Zimbabwe 7-6(12), 6-7(3), 6-3, 6-3 to win the title.

With the victory, Nestor completed the career doubles grand slam, holding all four majors in his trophy cabinet.

Incredibly, the pair would successfully defend their Wimbledon crown in 2009, winning it a second time by defeating the Mike and Bob Bryan brothers in a four-set final.