John Holden has been competing at the event for 14 years and has dreamt of winning since he attended the race as a child.
But in nail-biting defeats, the 51-year-old and his partner Andy Winkle were beaten by winners Nick Crowe and Mark Cox in both of the Sure Mobile sidecar races this year.
Holden gained 2nd and 3rd places in the A and B races, achieving the silver medal overall after making a combined time of 2:00:01·57, just over a minute more than Crowe and Cox with 1:58:57·56.
Holden led the race in his LCR Suzuki 600cc bike for the first one and a half laps, and achieved his best average speed, reaching 113.75mph.
The pair beat former world champions Tim Reeves, who came third, and Klaus Klaffenbock. They also won medals for their part in the LCR manfacturing team.
He said: "I was gutted that we didn't win. The competition was probably a little bit tougher than last year.
"But we've been quite fortunate. We've got a good bike and good people around us. It's just racing and things go wrong. I wouldn't put it down to bad luck.
"I've just got to keep trying. I've won races all over the place but I've been going to the TT since I was a child and have watched people that are famous racing there. To be there and be successful is good but to go there and win would be something else."
Holden and Winkle, who won the European championship last year, are now concentrating their efforts on the British Championships.
They are already leading the competition, having won the first two rounds, and will travel to Snetterton to take part in the third round in July.
They are also planning to return to the Isle of Man in July for the Southern Hundred races in Castletown, in preparation for next year's TT.
Holden added: "I've decided I'm going again competitively and then I will see. My son George has a bike and wants to race. He's 16 next April so that might be the turning point for my career. I might stop and help him instead."
Holden thanked sponsors Johnson Matthey, who he works for, Proflex Suspension, James Alpe, D&A Walmsley and David Johnston Builders.
He also thanked his family and friends for their support, including his partner Fiona Baker-Milligan, who also enjoys racing and came 17th with her father Tony Baker.