As we reach the business end of the season, the former Bournemouth, West Ham United, Portsmouth and Southampton gaffer will certainly feel that his side's progression to the quarter-finals has hampered their chances of Champions League qualification for a second successive campaign.
Thanks to a late Peter Crouch goal, Spurs defeated AC Milan at the San Siro in mid-February. Since then, the north London side have picked up just eight points from eight Premier League fixtures, winning only once. They have slipped down from fourth position into sixth, leaving them seven points adrift of Manchester City, who occupy the final Champions League place, with four games remaining.
Realistically, Spurs are left fighting for a Europa League place with Liverpool. And, with trips to Eastlands and Anfield to come, their hopes of even taking that spot are becoming increasingly remote.
It could be argued that Redknapp was short-sighted, chasing silverware in Europe's elite club competition at the expense of Tottenham's long-term future. Maybe his main focus should have been on retaining their Champions League berth, rather than going all-out to win it.
By failing to keep hold of their place, not only will Spurs miss out financially, but Redknapp may struggle to attract the same calibre of player he did during the previous summer. Current squad members like Gareth Bale and Rafael Van der Vaart may even look to jump ship. If this does prove to be the case, their will be concern that they'll be left behind by big-spending City, a team who were undoubtedly seen as their direct rivals for fourth position.
Regardless, Redknapp will have no regrets. It's not like him to approach a competition, especially of the Champions League's magnitude, half-heartedly. Spurs made a huge impression, topping arguably the toughest group whilst playing a fearless brand of attacking football. The club's fans enjoyed several memorable trips abroad, as well as some magical nights at White Hart Lane, watching their team brush aside FC Twente, Inter Milan and Werder Bremen.
Spurs were never expected to reach the Champions League last year, particularly considering they finished level on points with West Ham in eighth the season before. Now, expectation levels have been raised.
Although the Europa League seems insignificant after having a taste of the Champions League, it's vital that Spurs beat Liverpool into fifth position, if not only to give them a greater chance of hanging onto their star men. Redknapp will already be thinking about potential signings too, and will see the Europa League, no matter how lowly its credibility may seem, as a key negotiating tool for certain targets.
Over the past three years, Redknapp has developed Spurs into a real force to be reckoned with, enhancing his own reputation at the same time. Now, it's imperative he keeps that level of performance up. By qualifying for the Europa League, it'll give Redknapp more of an opportunity to improve on his existing squad as they look to recapture their place challenging amongst European football's elite.