Patrick Bamford had been struggling for fitness after taking a knock on his ankle in the 1-0 defeat of Norwich at Carrow Road in April. He was nursed through the final games of the season and sat out the second leg semi-final win over Brentford in the hope that he would be ready for the big stage of Wembley.
It was a punt that backfired as Bamford failed to pose any threat to Norwich's goal in the Wembley defeat and looked a frustrated figure as he and his teammates couldn't get a foothold in the game.
21-year-old Bamford has tasted play-off heartbreak for the second season running after his substitute appearance for Derby County last season failed to inspire an equaliser as QPR claimed a fortunate Wembley win. Bamford's 25 goals last season - split between loan spells with both MK Dons and Derby - were followed by 19 in the 2014-15 campaign and the Chelsea loanee had played a major part in 'Boro staying in and around the promotion race in the Sky Bet Championship.
Bamford's goals had alerted a string of potential suitors, but a timid Wembley performance against Norwich on Monday may have some of them thinking twice.
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In truth, 'Boro fans may take a small crumb of comfort from that, as Bamford's ankle injury clearly played a part in his anonymity at Wembley, and may lead to the Riversiders having a chance of securing his services again.
Bamford's performance may lead to some Barclays Premier League clubs choosing not to follow up their leads. Equally, Bamford's parent club Chelsea - where he has only recently signed a new five-year contract - may be unsure whether he is ready to battle for a first team place at Stamford Bridge.
The Grantham-born striker mustered just one shot on goal on Monday, a tame prod straight at Norwich 'keeper John Ruddy on 68 minutes, and had only 23 touches of the ball, roughly one every four minutes.
This highlights how Middlesbrough failed to get the ball into dangerous areas and despite Bamford's hard running, how he failed to maintain possession when he had it.
Bamford's strike partner Jelle Vossen didn't fare much better, although he hit the bar with a first half strike with the score at 0-0. However, with 'Boro making little impact, Aitor Karanka switched the Belgian Vossen for Spanish striker Kike mid-way through the second half, with little success.
Karanka persevered with Bamford, but 'Boro's lack of cutting edge was a significant factor in the crushing 2-0 defeat, and while injury can explain Bamford's lack of impact on the big occasion, it was a gamble that didn't pay off.