The defender has also proven his quality against some of the best in the world, doing so for both Southampton, England and Manchester United.
Shaw spent nine years in the Southampton academy before making his first-team debut in 2012 during an FA Cup tie against Millwall.
Throughout his domestic endeavours, Eden Hazard was one of his most frequent opponents with ten meetings across all competitions.
The recently retired Chelsea legend scored twice while up against Shaw, who was on the winning side just once for Southampton and United across their meetings.
Fellow Southampton academy graduate and eventual five-time Champions League winner Gareth Bale came up against him for the first time in May 2013, scoring in Tottenham's 1-0 win.
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They shared the pitch for a second time eight years later when Shaw was at United before England and Wales' 2022 World Cup clash.
World Cup winner Lionel Messi has been an opponent just once when he and Barcelona faced United in the Champions League quarter-finals.
Although the footballing magician didn't score or assist, it was Shaw's own-goal that helped the Catalan giants win on aggregate in 2019.
But there is another player who stands out for the left-back.
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During his first full senior season, Southampton welcomed Chelsea in the FA Cup third round and fell to a 5-1 defeat.
Legends including Ashley Cole and Frank Lampard both featured for the Blues but the performance from Victor Moses sticks out above the rest.
"People always think I'm joking, but one of my hardest games ever was against Moses when I was coming in as a 17-year-old at Southampton," he told the United website in 2020.
"Maybe because I was so young. He was really quick, direct, strong and that was a challenge for me.
"I've played against the likes of Bale, Messi and Hazard, and they were all so good, but I always remember Moses as a really tough opponent as well."
Moses, now of Spartak Moscow, is somewhat of a cult hero at Chelsea after he starred in their 2016/17 Premier League triumph, excelling at right wing-back under Antonio Conte.
His aforementioned goal against Southampton was a well-executed half-volley, and Shaw could only stand and watch it fly into the net.
The duo met yet again later in the campaign and a third and final time in 2013 when Moses was on loan at Liverpool.
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However, his FA Cup debut for Chelsea made a great impression on Shaw, seemingly more so than domestic and international icons.
Shaw could look back and change his opinion on his toughest opponents when he retires but until then, even amid the abundance of world-class talent he's faced, Moses looks set to stay at the top.