Click here to watch Matt de Boer's interview with Milestone Man Ryan Crowley

Ahead of his 150th AFL game, Fremantle’s master tagger Ryan Crowley has nominated some of his toughest opponents over the journey.

Crowley began his career as a midfielder/forward, but a role change in 2005 saw him take up the art of negating opponents.

The arrival of Ross Lyon as senior coach for the 2012 season saw Crowley take his tagging to a new level.

The former Saint Kilda boss had a history of turning serviceable players into elite stoppers, with Saints Steven Baker and Clinton Jones among the AFL’s best at the role during Lyon’s stint there.

Crowley, who won Freo’s Doig Medal in 2012, has rarely been beaten over the past season and a half.

He nominated a couple of Sydney Swans’ veterans among his hardest opponents, but for differing reasons.

“Ryan O’Keefe is one of the hardest runners I’ve ever played on,” Crowley said of the 2012 Norm Smith Medallist.

“Then you’ve got a guy like Adam Goodes, who can take you from zone to zone and expose you in so many different ways.”

Some of Crowley’s most challenging match-ups involved players who possessed the ability to find the leather.

“The guys who are magnets, like Lenny Hayes, Simon Black and Shane Crawford,” he said.

Players who don’t need many touches to hurt opposition sides have also provided Crowley with some stern tests.

“Chris Judd, when he was up and really firing back in the West Coast days, was amazing,” Crowley said.

Of the newer generation of midfielders, Adelaide’s Patrick Dangerfield is one that can’t be afforded too many possessions.

The sides have met four times in the past year, although Crowley has only tagged the Crow in the two most recent encounters.

While he performed well on Dangerfield in last year’s semi-final, the brilliant Adelaide midfielder wielded a big influence in the round 10 match this year, but not through sheer volume of possession.

Dangerfield attempted to break Crowley’s tag by dragging him deep into Adelaide’s forward 50, where he kicked three important goals.

“Trying to play on him out of the goal square, I probably learnt more in a 20-30 minute spell playing on him there than I have out of most guys,” Crowley said.

Two of Dangerfield’s goals came early in the game, which Crowley said was a tagger’s nightmare.

“I had a headache after the game, because if he gets a couple early, for the rest of the game, you’re almost scared,” he said.

“It was a really draining game… you’ve got to be ready for those sorts of things.”

But as for his toughest opponent, Geelong Brownlow Medallist and current Gold Coast captain Gary Ablett Jnr gets the nod.

“I’ve had some good tussles with him over the years,” Crowley said.

“He’s got so many strings to his bow.”