At least not so far. Not only has the 24-year-old Hamilton Academical midfielder been deemed fit enough to start just eight matches during this campaign due to a knee problem, the Scouser watched his beloved Liverpool self-combust in the final few weeks of the season, then saw former club Wigan crash out to QPR in the English Championship play-offs during the week, days after his own club's promotion bid fell short behind Dundee on the last day of the season by a mere two points.
Salvation, however, could still be lurking around the corner. Victory against Falkirk this afternoon would see Hamilton enter a two-legged play-off against Hibernian, handing Routledge the chance to return triumphantly to the Scottish top flight which he graced with Accies back in 2010.
"Liverpool were a bit like Hamilton, to be honest," he said. "For so long you thought they were going to do it, then towards the end a few little bad results crept in and they just missed out. I don't really get to too many games these days, but overall I was just made up for the way they played; they brought the enjoyment back to the games and that was what all Liverpool fans wanted.
"I have a couple of mates at Wigan and they have also had a good season, even though they missed out in the play-offs. But this is the main one for Accies. As long as we can get up [to the SPFL Premiership] that is all that matters."
Routledge spent 10 years at Liverpool's academy - occasional full-back Martin Kelly is the closest of his remaining friends there - then made just one last-minute substitute appearance during his entire two-and-a-half year Wigan career.
He swapped Lancashire for Lanarkshire in 2010, moving in the opposite direction from Jameses McCarthy and McArthur, who pitched up at the DW Stadium a year apart. Routledge initially came north on a temporary basis, having previously on loan at Swedish side Ostersunds SK, ironically the club where his former manager at Hamilton, Billy Reid, now finds himself as assistant.
Routledge is in his fourth stint at New Douglas Park and Wigan's loss has been Hamilton's gain. Injury plagued or not, Routledge's flair for the unseen, unselfish parts of the game will be crucial today, especially given manager Alex Neil's ongoing suspension. The best statistic doing the rounds in the wake of the 1-1 first-leg draw at Falkirk was that Hamilton created more shots on goal than they did in their 10-2 dismantling of Morton.
"Sometimes you wonder what would have happened if I had stayed [at Wigan], but I needed to get out and try to get first-team games," Routledge said. "Off and on I have been here for about four years and it is a great club to play for, I just want to bring success to them if I can.
"This is my first time in a play-off and it is tight. Falkirk are a very good team, and all our games throughout the season have been very tight. Both teams have good quality, so I think no matter who goes through the matches against Hibs would be quite even. But first we have got to get through."
No-one has a greater appreciation of what Routledge is capable of bringing to the table than his manager. Neil has made a career doing precisely the same kind of gritty midfield chores and he feels the Scouser is one of many in his squad who could compete at Premiership level. The home and away meetings between the victor of this tie and Hibs will both be carried live, one on BT Sport and one on Sky.
"It has been a hard season for Jon, but I have been there myself in terms of injuries," Neil said. "He missed a lot of the season, but he does a great job and that role is very important. I have done it for years and years, and no-one gives you plaudits for it, but when you become a manager you realise how important it is.
"We have a few players who have played the Premier League - albeit a few years ago - and I am desperate for them to go and showcase their talent on a bigger stage. If we manage to beat Falkirk and play Hibs, that will give them the chance to do that. I played at Premier League level and this group is good enough to do that."