The centre-back started both legs of the 2016 final as Falkirk saw a 1-0 first-leg lead disintegrate at Kilmarnock with a 4-0 thumping. The following season he was part of a defence that surrendered a late lead to Dundee United in the semi-finals. Then a year later he joined the Tannadice club and would play the part of bemused bystander as four consecutive United team-mates missed spot-kicks in the final against St Mirren.
United would make up for that famous disappointment last term with a triumphant march toward the title, but Watson again missed out on the elite of Scottish football as he was allowed to leave in the summer. Now halfway through a two-year deal with Dunfermline Athletic, he’s hoping that his familiarity with the mini-tournament can help inspire the Fife club to do what no second-tier side has yet by winning the play-offs from fourth place.
Ahead of tonight’s quarter-final first-leg encounter with local rivals Raith Rovers, the 30-year-old said: “I think I’ve had every experience in the play-offs now - an early exit, getting to the final and winning the first-leg before getting battered in the second-leg. Then at Dundee United, we drew and went all the way to penalties - and I’ve never seen a penalty shoot-out like that since. It’s the toughest way to end the season.
"I don’t think there’s many boys who have experienced the play-offs in our group, so I’ve been trying to give little bits of advice to them in certain areas.
“We can’t win the game on Tuesday night, it’s two ties, so it’s just about staying in the game and taking it to Saturday.”
There won’t be much of a fighting chance for the return leg if the Pars succumb to the type of hammering they received on the last visit to Stark’s Park, losing 5-1 at the end of March. Watson, who missed that encounter, insists things will be different this time.
He said: “I was at the game, I was there, but I didn’t play. As a group, we got it wrong on the day. We won’t be making that mistake again, certainly.”